Compounds with an acceptor and a donor group

ABSTRACT

The present invention describes compounds having an acceptor group and a donor group, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.

The present invention describes compounds having an acceptor group and adonor group, especially for use in electronic devices. The inventionfurther relates to a process for preparing the compounds of theinvention and to electronic devices comprising these compounds.

Light-emitting electronic components are increasingly coming intoeveryday use as light sources. Their advantages are low energyconsumption, a compact design and a much longer lifetime compared toconventional means of lighting. While inorganic light-emitting diodeswere the first to be used as means of lighting, organic light-emittingdiodes (OLEDs) have also increasingly found use in articles for everydayuse, for example in displays for mobile phones. Advantages of the OLEDsover their inorganic equivalents lie in easier processibility. Thematerials used in OLEDs can be dissolved in suitable solvents. Theindividual layers of the components can be applied to a substrate, forexample, by means of printing methods. It is therefore comparativelysimple to produce curved displays. Since the layers are not incrystalline form, OLEDs are flexible compared to LEDs based on inorganiccompounds and can therefore also be applied to flexible substrates forthe production of flexible screens. OLEDs themselves emit light andtherefore do not require any backlighting, as required in the case ofliquid-crystal displays (LCDs) for instance. It is thus possible to makescreens based on OLEDs very thin. A further advantage exhibited bydisplays based on OLEDs is very high contrast, since non-excited OLEDsdo not emit any light, i.e. are completely black. In terms of lightyield, great advances have been achieved, and so it is now possible toconvert the energy used to induce electronic states of the OLEDvirtually completely to light.

OLEDs are formed from multiple layers. First of all, an anode is appliedto a substrate, which is preferably transparent, for example a glassplate or a transparent polymer film. Indium tin oxide (ITO) is usuallyused here to obtain a transparent anode. Then a hole transport layer(HTL) is applied to the anode. In order to facilitate the transfer ofholes from the anode to the hole transport layer, i.e. to lower theinjection barrier for holes, an interlayer composed of PEDOT/PSS(poly(3,4-ethylenedioxythiophene) doped with polystyrenesulfonate) isoften first applied to the anode before the hole transport layer is thenapplied. The hole transport layer is then followed by an emitter layer(EL) containing or based on a dye in a proportion of, for example, 5% to10% by weight. To the latter may then be applied an electron transportlayer (ETL). Finally, under high vacuum, a cathode consisting of a metalor an alloy having a low electron work function, for example calcium,aluminium, barium, ruthenium, magnesium/silver alloy, is applied byvapour deposition. As a protective layer and to reduce the injectionbarrier for electrons, it is also possible to apply a very thin layer oflithium fluoride, caesium fluoride or silver between the cathode andETL. The structure of the OLEDs is thus relatively complex and entailsmultiple operating steps. Moreover, the materials used are sensitive tomoisture and oxygen, and so the structure has to be encapsulated inorder to ensure that the OLED will be able to function over a prolongedperiod.

Electrons are injected into the layer structure from the cathode andholes from the anode as charge carriers. Electrons and holes drifttoward one another and in the emitter layer in order to form a boundstate which is referred to as an exciton. In the recombination of thecharge carriers, singlet and triplet excitons are formed in a ratio of1:3. The decay of the exciton provides the energy for the excitation ofthe dye molecule. The excited state can then return to the ground stateand in so doing emit a photon. In the case of emission from the singletstate, which is referred to as fluorescence, only a maximum of 25% ofthe excitons generated lead to emission, while the radiationlesstransitions that proceed from the triplet state are lost in the form ofheat. The transition from the triplet state T₁ to the singlet state S₀is highly spin-forbidden and is therefore not available for emission oflight.

In the case of triplet emission, which is referred to asphosphorescence, it is theoretically possible by means of tripletharvesting to utilize all excitons and emit them as light. In this case,the additionally induced singlet state at an energy above the tripletstate is fully relaxed to the triplet state by intersystem crossing.

Triplet emitters used are usually transition metal complexes in whichthe metal is chosen from the third period of the transition elements,for example iridium, platinum or else gold. As a result of the highspin-orbit coupling of the central noble metal ions, the triplet-singlettransition which is strictly forbidden for optical transitions isallowed and the emission lifetime of a few μs which is suitable for usein OLEDs is achieved. With growing current densities and the resultingpopulation of a majority or all triplet states T₁ of the emittermolecules, however, saturation effects arise and, as a result, chargecarrier streams can no longer be utilized fully for population ofexcited states, meaning that ohmic losses arise and the efficiency ofthe emitter falls (“roll-off” characteristics).

Singlet emitters have a much shorter emission lifetime in the region ofnanoseconds, and so roll-off effects occur to a much lesser degree, ifat all. The efficiency of the emitters or the quantum yield can beincreased by utilizing triplet states as well for the emission of light.For this purpose, however, the energy difference between the highestoccupied triplet state T₁ and the lowest excited singlet state S₁ has tobe small, such that thermal repopulation of the singlet state S₁ fromthe triplet state T₁ is possible at room temperature. Moreover, strongspin-orbit coupling has to be enabled, such that intersystem crossingenables the spin-forbidden T₁→S₁ transition. The emission lifetime forthis transition should be in the region of less than 1 μs, for exampleabout 100 to 600 ns.

In singlet harvesting, as in the case of triplet harvesting, it is thusthe lowest excited singlet state which is populated. However, theemission is not from the lowest triplet state T₁ but via thermalrepopulation from the lowest excited singlet state S₁, such that theexcitation energy that would otherwise be lost is almost completelyavailable to the triplet state for the emission of light.

This process is referred to as thermally activated delayed fluorescence(TADF) and is described, for example, by B. H. Uoyama et al., Nature2012, Vol. 492, 234. In order to enable this process, a comparativelysmall singlet-triplet separation ΔE(S₁−T₁) of less than about 2000 cm⁻¹,for example, is needed in the emitter. In order to open up the T₁→S₁transition which is spin-forbidden in principle, as well as the emitter,it is possible to provide a further compound in the matrix that hasstrong spin-orbit coupling, such that intersystem crossing is enabledvia the spatial proximity and the interaction which is thus possiblebetween the molecules, or the spin-orbit coupling is generated by meansof a metal atom present in the emitter.

Suitable emitters are in particular molecules which exhibit high chargetransfer character, for example copper compounds. A highly luminescentcompound that exhibits thermally activated delayed fluorescence thus hasto be configured such that it has a very small separation ΔE(S₁−T₁)coupled with relatively short decay rates of >10⁶ s⁻¹, such that thereis a decline in competing decay pathways where there is no emission oflight.

A further light-emitting electronic component which has been developedis organic light-emitting electrical cells (OLECs, also called LECs orLEECs). OLECs were described for the first time by Ouibing Pei et al.,Science, 1995, 296, 1086-1088, where the underlying principles are alsoelucidated.

By comparison with OLEDs, OLECs have a simpler structure and are alsosimpler to produce. For instance, OLECs can have a smaller number oflayers compared to OLEDs. In addition, the active layer can be thickerin OLECs, and so it is possible to use simpler processes for producingthe active, light-emitting layer. The active light-emitting layer inOLECs can have a thickness of several micrometres up to several tens ofmicrometres. Application of the active layer can therefore beaccomplished using processes such as inkjet printing, screen printing orspray coating, which are also suitable for inexpensive mass production.By comparison with OLEDs, OLECs exhibit lower sensitivity toirregularities of the substrate surface and to defects in the activelayer. OLECs therefore have better suitability for production oflarge-area light-emitting devices.

An OLEC comprises two electrodes and an active layer arranged betweenthe cathode and anode. The active layer comprises a light-emittingorganic semiconductor and an electrolyte which provides mobile ions. Inorder to enable the exit of light, at least one of the electrodes shouldbe transparent.

Light-emitting organic semiconductors used may be conjugated copolymersor ionic transition metal complexes as also used in OLEDs, for example.Illustrative transition metal complexes aretris(2-phenylpyridine)iridium (Ir(ppy)₃) ortris(8-hydroxyquinoline)aluminium (Alq₃). Small molecules offer theadvantage that they are easier to process, since they can more easily bedissolved in a suitable solvent. However, in the processing of thesesolutions, the difficulty of poor film-forming properties can arise.

The ability of the organic semiconductor to emit light is determined bythe energy of the highest occupied molecular orbital (HOMO) and of thelowest unoccupied molecular orbital (LUMO) and their relative positions.In the case of organic semiconductors, however, HOMO and LUMO can beadjusted in terms of their energy by introducing side chains in themolecule or preparing copolymers from different organic semiconductors,such that different organic semiconductors are present in the copolymerchain. In this way, it is also possible to influence the solubility ofthe organic semiconductor and the film-forming properties thereof.However, the interaction between the orbitals by which the position ofthe energy states is determined is also affected by the geometry of thepolymer and the relative position with respect to other molecules. Inthe case of films which are produced from solutions, therefore, a changein the solvent can affect the position of the HOMO and LUMO, such thatthe emission of an organic light-emitting component has a relativelybroad spectrum owing to the amorphous character of the film.

Most metals have a relatively high work function, and for that reasonthere is considerable expenditure of energy at the electrodes in orderto inject electrons from the electrode material into the organicsemiconductor. In the case of use of alkali metals or alkaline earthmetals, these metals do have a low work function, such that the energydifferential between the cathode and the LUMO of the organicsemiconductor is reduced. However, these metals are very reactive towardoxygen and water, and so the production of the electronic components iscomplex.

In the case of organic light-emitting electrochemical cells, mobile ionsare utilized in order to enable the transfer of charge from theelectrode into the active layer. If a voltage is applied between thecathode and anode, positive ions accumulate at the cathode and negativeions at the anode, such that an electrical double layer is formed. Theelectrical double layers are very thin, which means that a highelectrical field gradient builds up at the interface to the electrodeirrespective of the layer thickness of the active layer. If there is asufficiently great potential difference between the electrodes, theelectrical double layer enables efficient injection of charge carriersinto the HOMO or LUMO of the organic semiconductor. The injection ofcharge carriers is compensated for by an opposing movement of chargedions. The injection of electrons at the cathode therefore brings aboutan accumulation of positive ions and hence causes n-doping. Theextraction of electrons at the anode or the injection of holes at theanode is correspondingly compensated for by negatively charged ions andbrings about p-doping. The electrochemical doping facilitates thetransport of electrons or holes within the organic semiconductor. In thecase of thicker active layers too that bring about a greater electrodeseparation, it is therefore possible to bring about effective chargetransport with a small potential difference.

The electrochemically doped regions grow in the direction of one anotheruntil they ultimately meet, and pn recombination is brought about in avery thin undoped layer. However, there is a crucial difference in themechanism of charge transport in OLECs and OLEDs. While the charges inOLECs are transported with the aid of mobile ions, the charge istransported in OLEDs by hopping of electrons/holes from more or lessstationary molecules. In addition, OLEDs often contain further layers(for example electron and hole transport layers) having differentmaterials. The OLEC, by contrast, in production, requires merely theprovision of a single homogeneous active layer since the layers for theelectron and hole transport form automatically in the active layer afterapplication of a potential difference between the electrodes. Bycomparison with OLEDs, therefore, the function of the OLEC does notdepend on the work function of the electrodes. Thus, both electrodes canbe produced from the same material. It is thus also possible to producea completely metal-free OLEC.

OLEDs are diodes having a forward and reverse direction for the chargetransport, meaning that the current-voltage curves are unsymmetric.OLECs are essentially an electrolytic cell. After application of apotential difference, the electrolyte is oxidized at the anode andreduced at the cathode.

OLECs are typically produced with a single solution comprisinglight-emitting and charge-transporting conjugated polymers, for examplepolyphenylene-vinylene polymers, polythiophene polymers or polyfluorenepolymers, and an electrolyte system comprising mobile ionic dopants, forexample lithium triflate, and compounds that form the electrolyte, forexample polyethylene oxide.

Light-emitting electrochemical cells are known, for example, from WO2013/173845.

If a singlet emitter is used as the dye, analogously to the processes asdescribed above for OLEDs, the energy released in triplet transitions islost in the form of heat. Since only about 25% of the recombinations ofcharge carriers lead to singlet excitons, this means that 75% of allcharge carriers which are injected into the active layer are lost togeneration of light. The efficiency in relation to the light yield isthus unsatisfactory in LECs of this kind. It is known in the prior artthat OLEDs are distinctly superior to the OLECs with regard to lifetimeand efficiency.

One problem addressed by the invention was therefore that of providingorganic electroluminescent devices (OLEDs, PLEDs) or organiclight-emitting electrochemical cells (OLECs) which achieve a high lightyield with the electrical energy used and overcome the disadvantagesknown from the prior art.

A further problem addressed by the present invention is that ofproviding compounds which are suitable for use in an organic electronicdevice, especially in an organic electroluminescent device or an organicelectrochemical cell, and which lead to good device properties when usedin this device, and that of providing the corresponding electronicdevice.

More particularly, the problem addressed by the present invention isthat of providing compounds which lead to a high lifetime, goodefficiency and low operating voltage. Particularly the properties of thematrix materials too have an essential influence on the lifetime andefficiency of the organic electroluminescent device.

A further problem addressed by the present invention can be consideredthat of providing compounds suitable for use in a phosphorescent orfluorescent OLED, especially as a matrix material. It is a particularobject of the present invention to provide matrix materials suitable forred-, yellow- and green-phosphorescing OLEDs and possibly also forblue-phosphorescing OLEDs.

Moreover, the compounds should be processible in a very simple manner,and especially exhibit good solubility and film formation. For example,the compounds should exhibit elevated oxidation stability and animproved glass transition temperature.

A further object can be considered that of providing electronic deviceshaving excellent performance very inexpensively and in constant quality.

Furthermore, it should be possible to use or adapt the electronicdevices for many purposes. More particularly, the performance of theelectronic devices should be maintained over a broad temperature range.

It has been found that, surprisingly, particular compounds that aredescribed in detail hereinafter solve these problems and eliminate thedisadvantage from the prior art. The use of the compounds leads to verygood properties of organic electronic devices, especially of organicelectroluminescent devices, especially with regard to lifetime,efficiency and operating voltage. The present invention thereforeprovides electronic devices, especially organic electroluminescentdevices or organic light-emitting electrochemical cells, comprisingcompounds of this kind, and also the corresponding preferredembodiments.

The present invention therefore provides a compound comprising at leastone structure of the following formula (I):

where the symbols used are as follows:

-   -   Q is an acceptor group comprising an aromatic or heteroaromatic        ring system which has 5 to 60 aromatic ring atoms and may be        substituted by one or more R¹ radicals;    -   HL is a donor group;    -   Ar^(a), Ar^(b) is the same or different and is an aromatic or        heteroaromatic ring system which has 5 to 60 aromatic,        preferably 5 to 40 aromatic, ring atoms and may be substituted        by one or more R¹ radicals;    -   R^(a), R^(b) is the same or different and is H, D, F, Cl, Br, I,        B(OR¹)₂, CHO, C(═O)R¹, CR¹═C(R¹)₂, CN, C(═O)OR¹, C(═O)N(R¹)₂,        Si(R¹)₃, N(R¹)₂, NO₂, P(═O)(R¹)₂, OSO₂R¹, OR¹, S(═O)R¹,        S(═O)₂R¹, a straight-chain alkyl, alkoxy or thioalkoxy group        having 1 to 40 carbon atoms or a branched or cyclic alkyl,        alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of        which may be substituted by one or more R¹ radicals, where one        or more nonadjacent CH₂ groups may be replaced by —R¹C═CR¹—,        —C—C—, Si(R¹)₂, Ge(R¹)₂, Sn(R¹)₂, C═O, C═S, C═Se, C═NR¹, NR¹,        P(═O)(R¹), —C(═O)O—, —C(═O)NR¹—, —O—, —S—, SO or SO₂ and where        one or more hydrogen atoms may be replaced by D, F, Cl, Br, I,        CN or NO₂, or an aromatic or heteroaromatic ring system which        has 5 to 60 aromatic, preferably 5 to 40 aromatic, ring atoms        and may be substituted in each case by one or more R¹ radicals,        or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic,        preferably 5 to 40 aromatic, ring atoms and may be substituted        by one or more R¹ radicals, or an aralkyl or heteroaralkyl group        which has 5 to 60 aromatic, preferably 5 to 40 aromatic, ring        atoms and may be substituted by one or more R¹ radicals, or a        diarylamino group, diheteroarylamino group or        arylheteroarylamino group which has 10 to 40 aromatic ring atoms        and may be substituted by one or more R¹ radicals; or a        combination of these systems; at the same time, the R^(a) and        R^(b) together or with the Ar^(a) or Ar^(b) group may form a        mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or        heteroaromatic ring system;    -   R¹ is the same or different at each instance and is H, D, F, Cl,        Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR²,        C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR²,        S(═O)R², S(═O)₂R², a straight-chain alkyl, alkoxy or thioalkoxy        group having 1 to 40 carbon atoms or a branched or cyclic alkyl,        alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of        which may be substituted by one or more R² radicals, where one        or more nonadjacent CH₂ groups may be replaced by —R²C═CR²—,        —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,        P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where        one or more hydrogen atoms may be replaced by D, F, Cl, Br, I,        CN or NO₂, or an aromatic or heteroaromatic ring system which        has 5 to 60 aromatic, preferably 5 to 40 aromatic, ring atoms        and may be substituted in each case by one or more R² radicals,        or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic,        preferably 5 to 40 aromatic, ring atoms and may be substituted        by one or more R² radicals, or an aralkyl or heteroaralkyl group        which has 5 to 60 aromatic, preferably 5 to 40 aromatic, ring        atoms and may be substituted by one or more R² radicals, or a        diarylamino group, diheteroarylamino group or        arylheteroarylamino group which has 10 to 40 aromatic ring atoms        and may be substituted by one or more R² radicals; or a        combination of these systems; at the same time, two or more,        preferably adjacent R¹ radicals together may form a mono- or        polycyclic, aliphatic, heteroaliphatic, aromatic or        heteroaromatic ring system;    -   R² is the same or different at each instance and is H, D, F, Cl,        Br, I, B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³,        C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³,        S(═O)R³, S(═O)₂R³, a straight-chain alkyl, alkoxy or thioalkoxy        group having 1 to 40 carbon atoms or a branched or cyclic alkyl,        alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of        which may be substituted by one or more R³ radicals, where one        or more nonadjacent CH₂ groups may be replaced by —R³C═CR³—,        —C—C—, Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se,        C═NR³, NR³, P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂        and where one or more hydrogen atoms may be replaced by D, F,        Cl, Br, I, CN or NO₂, or an aromatic or heteroaromatic ring        system which has 5 to 60 aromatic, preferably 5 to 40 aromatic,        ring atoms and may be substituted in each case by one or more R³        radicals, or an aryloxy or heteroaryloxy group which has 5 to 60        aromatic, preferably 5 to 40 aromatic, ring atoms and may be        substituted by one or more R³ radicals, or an aralkyl or        heteroaralkyl group which has 5 to 60 aromatic, preferably 5 to        40 aromatic, ring atoms and may be substituted by one or more R³        radicals, or a diarylamino group, diheteroarylamino group or        arylheteroarylamino group which has 10 to 40 aromatic ring atoms        and may be substituted by one or more R³ radicals, or a        combination of these systems; at the same time, two or more,        preferably adjacent R² substituents together may also form a        mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or        heteroaromatic ring system;    -   R³ is the same or different at each instance and is H, D, F or        an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical        having 1 to 20 carbon atoms, in which hydrogen atoms may also be        replaced by F; at the same time, two or more, preferably        adjacent R³ substituents together may also form a mono- or        polycyclic, aliphatic, heteroaliphatic, aromatic or        heteroaromatic ring system.

Adjacent carbon atoms in the context of the present invention are carbonatoms bonded directly to one another. In addition, “adjacent radicals”in the definition of the radicals means that these radicals are bondedto the same carbon atom or to adjacent carbon atoms. These definitionsapply correspondingly, inter alia, to the terms “adjacent groups” and“adjacent substituents”.

The wording that two or more radicals together may form a ring, in thecontext of the present description, shall be understood to mean, interalia, that the two radicals are joined to one another by a chemical bondwith formal elimination of two hydrogen atoms. This is illustrated bythe following scheme:

In addition, however, the abovementioned wording shall also beunderstood to mean that, if one of the two radicals is hydrogen, thesecond radical binds to the position to which the hydrogen atom wasbonded, forming a ring. This shall be illustrated by the followingscheme:

A fused aryl group, a fused aromatic ring system or a fusedheteroaromatic ring system in the context of the present invention is agroup in which two or more aromatic groups are fused, i.e. annelated, toone another along a common edge, such that, for example, two carbonatoms belong to the at least two aromatic or heteroaromatic rings, as,for example, in naphthalene. By contrast, for example, fluorene is not afused aryl group in the context of the present invention, since the twoaromatic groups in fluorene do not have a common edge. Correspondingdefinitions apply to heteroaryl groups and to fused ring systems whichmay but need not also contain heteroatoms.

An aryl group in the context of this invention contains 6 to 60 carbonatoms, preferably 6 to 40 carbon atoms, a heteroaryl group in thecontext of this invention contains 2 to 60 carbon atoms, preferably 2 to40 carbon atoms, and at least one heteroatom, with the proviso that thesum total of carbon atoms and heteroatoms is at least 5. The heteroatomsare preferably selected from N, O and/or S. An aryl group or heteroarylgroup is understood here to mean either a simple aromatic cycle, i.e.benzene, or a simple heteroaromatic cycle, for example pyridine,pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, forexample naphthalene, anthracene, phenanthrene, quinoline, isoquinoline,etc.

An aromatic ring system in the context of this invention contains 6 to60, preferably 6 to 40, carbon atoms in the ring system. Aheteroaromatic ring system in the context of this invention contains 1to 60, preferably 1 to 40, carbon atoms and at least one heteroatom inthe ring system, with the proviso that the sum total of carbon atoms andheteroatoms is at least 5. The heteroatoms are preferably selected fromN, O and/or S. An aromatic or heteroaromatic ring system in the contextof this invention shall be understood to mean a system which does notnecessarily contain only aryl or heteroaryl groups, but in which it isalso possible for two or more aryl or heteroaryl groups to beinterrupted by a nonaromatic unit (preferably less than 10% of the atomsother than H), for example a carbon, nitrogen or oxygen atom or acarbonyl group. For example, systems such as 9,9′-spirobifluorene,9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. shallthus also be regarded as aromatic ring systems in the context of thisinvention, and likewise systems in which two or more aryl groups areinterrupted, for example, by a linear or cyclic alkyl group or by asilyl group. In addition, systems in which two or more aryl orheteroaryl groups are bonded directly to one another, for examplebiphenyl, terphenyl, quaterphenyl or bipyridine, shall likewise beregarded as an aromatic or heteroaromatic ring system.

A cyclic alkyl, alkoxy or thioalkoxy group in the context of thisinvention is understood to mean a monocyclic, bicyclic or polycyclicgroup.

In the context of the present invention, a C₁- to C₂₀-alkyl group inwhich individual hydrogen atoms or CH₂ groups may also be replaced bythe abovementioned groups are understood to mean, for example, themethyl, ethyl, n-propyl, i-propyl, cyclopropyl, n-butyl, i-butyl,s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl,t-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl,2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl,2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl,1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl,1-bicyclo[2.2.2]octyl, 2-bicyclo[2.2.2]octyl, 2-(2,6-dimethyl)octyl,3-(3,7-dimethyl)octyl, adamantyl, trifluoromethyl, pentafluoroethyl,2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl,1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n-dec-1-yl,1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl,1,1-dimethyl-n-hexadec-1-yl, 1,1-dimethyl-n-octadec-1-yl,1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl,1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec-1-yl,1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl,1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)cyclohex-1-yl,1-(n-butyl)cyclohex-1-yl, 1-(n-hexyl)cyclohex-1-yl,1-(n-octyl)cyclohex-1-yl and 1-(n-decyl)cyclohex-1-yl radicals. Analkenyl group is understood to mean, for example, ethenyl, propenyl,butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl,cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. An alkynylgroup is understood to mean, for example, ethynyl, propynyl, butynyl,pentynyl, hexynyl, heptynyl or octynyl. A C₁- to C₄₀-alkoxy group isunderstood to mean, for example, methoxy, trifluoromethoxy, ethoxy,n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or2-methylbutoxy.

An aromatic or heteroaromatic ring system which has 5 to 60, preferably5-40, aromatic ring atoms and may also be substituted in each case bythe abovementioned radicals and which may be joined to the aromatic orheteroaromatic system via any desired positions is understood to mean,for example, groups derived from benzene, naphthalene, anthracene,benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene,perylene, fluoranthene, benzofluoranthene, naphthacene, pentacene,benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene,spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene,cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluorene,cis- or trans-dibenzoindenofluorene, truxene, isotruxene, spirotruxene,spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran,thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole,indole, isoindole, carbazole, indolocarbazole, indenocarbazole,pyridine, quinoline, isoquinoline, acridine, phenanthridine,benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline,phenothiazine, phenoxazine, pyrazole, indazole, imidazole,benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole,pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole,naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole,1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine,benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene,2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene,4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine,phenothiazine, fluorubine, naphthyridine, azacarbazole, benzocarboline,phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole,1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole,1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole,1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine,tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine,purine, pteridine, indolizine and benzothiadiazole.

In a preferred configuration, compounds of the invention can berepresented by structures of formula (I). Preferably, compoundscomprising structures of formula (I) have a molecular weight of not morethan 5000 g/mol, preferably not more than 4000 g/mol, particularlypreferably not more than 3000 g/mol, especially preferably not more than2000 g/mol and most preferably not more than 1200 g/mol.

In addition, it is a feature of preferred compounds of the inventionthat they are sublimable. These compounds generally have a molar mass ofless than about 1200 g/mol.

The HL group represents a donor group, this concept being known in thespecialist field, especially in relation to TADF materials.

The donor group D (also called donor substituent) in the present case isunderstood to mean a group which is an electron donor group. What ismeant by a donor group is well known to those skilled in the art. It ispreferable when the donor group has a positive inductive effect (+I)and/or a positive mesomeric effect (+M). The determination of theparameters with the aid of the Hammett equation is well known to thoseskilled in the art.

Suitable donor substituents are especially diaryl- or -heteroarylaminogroups and carbazole groups or carbazole derivatives, such asindenocarbazoles or indolocarbazoles. These groups may also have furthersubstitution.

In a further embodiment, the donor group is selected from arylaminogroups, preferably di- or triarylamino groups, heteroarylamino groups,preferably di- or triheteroarylamino groups, carbazole groups,preference being given to carbazole groups.

It may preferably be the case that the donor group HL comprises a groupand preferably is a group selected from the formulae (H-1) to (H-3)

-   -   where the dotted bond marks the attachment position and    -   Ar², Ar³, Ar⁴ are each independently an aryl group having 6 to        40 carbon atoms or a heteroaryl group having 3 to 40 carbon        atoms, each of which may be substituted by one or more R¹        radicals;    -   p is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2 or 3 and more        preferably 0, 1 or 2 and    -   Z is CR¹ ₂, SiR¹ ₂, C═O, N-Ar¹, BR¹, PR¹, POR¹, SO, SO₂, Se, O        or S, preferably CR¹ ₂, N-Ar¹, O or S, where the R¹ radical has        the definition given in Claim 1 and Ar¹ represents an aromatic        or heteroaromatic ring system which has 5 to 60 aromatic,        preferably 5 to 40 aromatic, ring atoms and may be substituted        in each case by one or more R¹ radicals, an aryloxy group which        has 5 to 60 aromatic, preferably 5 to 40 aromatic, ring atoms        and may be substituted in each case by one or more R¹ radicals,        or an aralkyl group which has 5 to 60 aromatic, preferably 5 to        40 aromatic, ring atoms and may be substituted in each case by        one or more R¹ radicals, where it is optionally possible for two        or more, preferably adjacent R¹ substituents to form a mono- or        polycyclic, aliphatic, heteroaliphatic, aromatic or        heteroaromatic ring system which may be substituted by one or        more R² radicals.

It may additionally be the case that the donor group HL comprises agroup and preferably is a group selected from the formulae (H-4) to(H-26)

-   -   where Y¹ represents O, S, C(R¹)₂ or NAr¹, the dotted bond marks        the attachment position, e is 0, 1 or 2, j is 0, 1, 2 or 3, h is        0, 1, 2, 3 or 4, p is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2        or 3 and more preferably 0, 1 or 2, Ar¹ and Ar² have the        definition given above, especially for formula (H-1) or (H-2),        and R¹ has the definition given above, especially for formula        (I).

Of the groups (H-1) to (H-26), preference is given to carbazole groups,especially the groups (H-4) to (H-26).

Preferably, the Ar² group in the formulae (H-1) to (H-26) may be aconnecting structure of the formula (LAr-1)

-   -   where X is the same or different at each instance and is N or        CR¹, preferably CR¹, or C if a group binds to X; the dotted bond        marks the attachment position and s is 0, 1, 2, 3, 4, 5 or 6,        preferably 0, 1, 2 or 3, more preferably 0, 1 or 2 and        especially preferably 0 or 1, where the R¹ radical has the        definition given above, especially for formula (I). Preferably,        the two attachment positions of the group shown in formula        (LAr-1) are in para positions. It is further preferable that the        index p in formula (H-1) to (H-26) is 1 and the index s in        formula (LAr-1) is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2 or        3, more preferably 0, 1 or 2 and especially preferably 0 or 1.

Preferably, not more than two X groups in formula (LAr-1) per ring areN. More preferably, the connecting structure of the formula (LAr-1)comprises not more than two nitrogen atoms, more preferably not morethan one nitrogen atom and especially preferably no nitrogen atom.Furthermore, preference is given to compounds which are characterized inthat, in formula (LAr-1), at least four X per ring and preferably all Xare CR¹, where preferably at most 4, more preferably at most 3 andespecially preferably at most 2 of the CR¹ groups that X represents arenot the CH group. More preferably, the connecting structure of theformula (LAr-1) comprises not more than two R¹ radicals that are not H,more preferably not more than one and especially none.

The Q group in formula (I) represents an acceptor group comprising anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted by one or more R¹ radicals. Acceptor groupshaving this property are widely known in the specialist field,especially in relation to TADF materials. It is preferable when theacceptor group has a negative inductive effect (−I) and/or a negativemesomeric effect (−M). The determination of the parameters with the aidof the Hammett equation is also well known to those skilled in the art.Suitable acceptor substituents are especially electron-deficientheteroaryl groups and aryl group substituted by electron-withdrawingsubstituents, where these groups may also have further substitution.Examples of preferred electron-deficient heteroaryl groups are selectedfrom the group consisting of triazines, pyrimidines, phosphine oxidesand ketones.

Furthermore, surprising advantages are exhibited by compounds comprisingat least one structure of formula (I) or preferred embodiments thereofin which the acceptor group Q comprises at least one structure selectedfrom the group of the pyridines, pyrimidines, pyrazines, pyridazines,triazines, quinazolines, quinoxalines, quinolines, isoquinolines,imidazoles and/or benzimidazoles, particular preference being given topyrimidines, triazines and quinazolines.

In a preferred configuration of the present invention, it may be thecase that the acceptor group is a group that can be represented by theformula (QL)

Q¹-L¹  Formula (QL)

-   -   in which L¹ represents a bond or an aromatic or heteroaromatic        ring system which has 5 to 60 aromatic, preferably 5 to 40        aromatic, ring atoms and may be substituted by one or more R¹        radicals, and Q¹ is an electron-withdrawing group, where R¹ has        the definition given above, especially for formula (I).

Preferably, the L¹ group is a connecting structure of the formula(LAr-2)

-   -   where X is the same or different at each instance and is N or        CR¹, preferably CR¹, or C if a group binds to X;    -   the dotted bond marks the attachment position and t is 0, 1, 2,        3, 4, 5 or 6, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2        and especially preferably 0 or 1, where R¹ has the definition        set out above, especially for formula (I). Preferably, the two        attachment positions of the connecting structure shown in        formula (LAr-2) are in para positions.

Preferably, not more than two X groups in formula (LAr-2) per ring areN. More preferably, the connecting structure of the formula (LAr-2)comprises not more than two nitrogen atoms, more preferably not morethan one nitrogen atom and especially preferably no nitrogen atom.Furthermore, preference is given to compounds which are characterized inthat, in formula (LAr-2), at least four X per ring and preferably all Xare CR¹, where preferably at most 4, more preferably at most 3 andespecially preferably at most 2 of the CR¹ groups that X represents arenot the CH group. More preferably, the connecting structure of theformula (LAr-2) comprises not more than two R¹ radicals that are not H,more preferably not more than one and especially none.

It may further be the case that the index p in formula (H-1) to (H-26)is 0, 1 or 2 and the index t in formula (LAr-2) is 0, 1 or 2.Preferably, the index s in formula (LAr-1) may be 0, 1 or 2 and theindex t in formula (LAr-2) may be 0, 1 or 2. It may further be the casethat the difference between the index s in formula (LAr-1) and the indext in formula (LAr-2) is not more than 2, preferably not more than 1 andespecially preferably 0.

Preferred compounds of formula (I) comprise at least one donor group offormulae (H-1) to (H-26) where the Ar² group is a connecting structureof the formula (LAr-1), and at least one acceptor group of formula (QL)where L¹ can be represented by a connecting structure of the formula(LAr-2) in which the index s in formula (LAr-1) and the index t informula (LAr-2) have the following values:

Index s in Index t in formula formula Compound (LAr-1) (LAr-2) Formula(I-1) 0 0 Formula (I-2) 1 1 Formula (I-3) 2 2 Formula (I-4) 0 1 Formula(I-5) 1 0 Formula (I-6) 1 2 Formula (I-7) 2 1 Formula (I-8) 3 3 Formula(I-9) 3 2 Formula (I-10) 2 3 Formula (I-11) 0 2 Formula (I-12) 2 0Formula (I-13) 3 1 Formula (I-14) 1 3

In a further configuration, it may be the case that the Q group detailedinter alia in the formula (I) or the electron-withdrawing Q¹ grouprepresents a heteroaromatic ring system, where the ring atoms comprise 1to 4 nitrogen atoms and the ring system may be substituted by one ormore R¹ radicals, but is preferably unsubstituted, where R¹ has thedefinition detailed above, especially for formula (I).

Furthermore, preference is given to compounds which are characterized inthat the acceptor group Q in formula (I) or the electron-withdrawing Q¹group is a heteroaromatic ring system having at least two fused ringswhich may be substituted by one or more R¹ radicals, but is preferablyunsubstituted, where the ring atoms of the at least two fused ringscomprise at least one nitrogen atom and preferably at least two nitrogenatoms, where R¹ has the definition set out above, especially for formula(I).

It may further be the case that the Q group detailed inter alia in theformula or the electron-withdrawing Q¹ group represents a heteroaromaticring system having 9 to 14 and preferably 10 ring atoms, which may besubstituted by one or more R¹ radicals, where R¹ has the definitiondetailed above, especially for formula (I), but is preferablyunsubstituted.

Preferably, the Q group detailed inter alia in the formula (I) or the Q¹group detailed in formula (QL) may be selected from structures of theformulae (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9)and/or (Q-10)

where the dotted bond marks the attachment position,

-   -   Q′ is the same or different at each instance and represents CR¹        or N, and    -   Q″ represents NR¹, O or S;    -   where at least one Q′ is N and/or at least one Q″ is NR¹ and    -   R¹ is as defined in Claim 1.

Preferably, Q in formula (I) or the Q¹ group detailed in formula (QL) isselected from structures of the formulae (Q-11), (Q-12), (Q-13), (Q-14)and/or (Q-15)

where the symbol R¹ has the definition given for formula (I) inter alia,X is N or CR¹ and the dotted bond marks the attachment position, where Xpreferably represents a nitrogen atom.

In a further embodiment, the Q group detailed inter alia in formula (I)or the Q¹ group detailed inter alia in formula (QL) may be selected fromstructures of the formulae (Q-16), (Q-17), (Q-18), (Q-19), (Q-20),(Q-21) and/or (Q-22)

in which the symbol R¹ has the definition detailed above for formula (I)inter alia, the dotted bond marks the attachment position and m is 0, 1,2, 3 or 4, preferably 0, 1 or 2, n is 0, 1, 2 or 3, preferably 0, 1 or2, and o is 0, 1 or 2, preferably 1 or 2. Preference is given here tothe structures of the formulae (Q-16), (Q-17), (Q-18) and (Q-19).

In a further embodiment, the Q group detailed inter alia in formula (I)or the Q¹ group detailed inter alia in formula (QL) may be selected fromstructures of the formulae (Q-23), (Q-24) and/or (Q-25)

in which the symbol R¹ has the definition set out above for formula (I)inter alia, and the dotted bond marks the attachment position.

In a further embodiment, the Q group detailed inter alia in formula (I)or the Q¹ group detailed inter alia in formula (QL) may be selected fromstructures of the formulae (Q-26), (Q-27), (Q-28), (Q-29) and/or (Q-30)

where X is N or CR¹, the symbol R¹ has the definition given above forformula (I) inter alia, the dotted bond marks the attachment position,where X preferably represents a nitrogen atom and Ar¹ represents anaromatic or heteroaromatic ring system which has 5 to 60 aromatic,preferably 5 to 40 aromatic, ring atoms and may be substituted in eachcase by one or more R¹ radicals, an aryloxy group which has 5 to 60aromatic, preferably 5 to 40 aromatic, ring atoms and may be substitutedby one or more R¹ radicals, or an aralkyl group which has 5 to 60aromatic, preferably 5 to 40 aromatic, ring atoms and may be substitutedin each case by one or more R¹ radicals, where it is optionally possiblefor two or more, preferably adjacent R¹ substituents to form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem, preferably a mono- or polycyclic aliphatic ring system, whichmay be substituted by one or more R² radicals.

Preferably, the Q group detailed inter alia in the formula (I) or the Q¹group detailed inter alia in formula (QL) may be selected fromstructures of the formulae (Q-31), (Q-32), (Q-33), (Q-34), (Q-35),(Q-36), (Q-37), (Q-38), (Q-39), (Q-40), (Q-41), (Q-42), (Q-43) and/or(Q-44)

in which the symbols Ar¹ have the definition set out above for formula(Q-26), (Q-27), (Q-28), (Q-29) or (Q-30) inter alia and R¹ has thedefinition set out above for formula (I) inter alia, the dotted bondrepresents the attachment position and m is 0, 1, 2, 3 or 4, preferably0, 1 or 2, n is 0, 1, 2 or 3, preferably 0 or 1, and I is 0, 1, 2, 3, 4or 5, preferably 0, 1 or 2.

Preferably, the symbol Ar¹ represents an aryl or heteroaryl radical,such that an aromatic or heteroaromatic group of an aromatic orheteroaromatic ring system is bonded directly, i.e. via an atom of thearomatic or heteroaromatic group, to the respective atom of the furthergroup, for example the carbon or nitrogen atom of the (Q-26) to (Q-42)groups shown above.

In a further preferred embodiment of the invention, Ar¹ is the same ordifferent at each instance and is an aromatic or heteroaromatic ringsystem having 6 to 24 aromatic ring atoms, preferably 6 to 18 aromaticring atoms, and is more preferably an aromatic ring system having 6 to12 aromatic ring atoms or a heteroaromatic ring system which has 6 to 13aromatic ring atoms and may be substituted in each case by one or moreR¹ radicals, but is preferably unsubstituted, where R¹ may have thedefinition given above, especially in formula (I).

Advantageously, Ar¹ in the formulae (Q-26) to (Q-42) represents anaromatic ring system which has 6 to 12 aromatic ring atoms and may besubstituted by one or more R¹ radicals, but is preferably unsubstituted,where R¹ may have the definition detailed above, especially for formula(I).

Preferably, the R¹ radicals in the formulae (Q-1) to (Q-44) do not forma fused ring system with the ring atoms of the heteroaryl group to whichthe R¹ radicals are bonded. This includes the formation of a fused ringsystem with possible R², R³ substituents which may be bonded to the R¹radicals.

Preferably, the R² radicals do not form a fused ring system with thering atoms of the aryl group or heteroaryl group Ar¹ to which the R²radicals in the formulae (Q-26) to (Q-42) may be bonded. This includesthe formation of a fused ring system with possible R³ substituents whichmay be bonded to the R² radicals.

In a preferred embodiment, it may be the case that theelectron-withdrawing Q¹ group is an aromatic or heteroaromatic ringsystem having 5 to 60, preferably having 5 to 40 and more preferablyhaving 6 to 24 aromatic ring atoms, especially preferably having 6 to 18aromatic ring atoms, and having one or more electron-withdrawingsubstituents.

Preferably, the electron-withdrawing substituent has a Hammett constant,σ, of not less than zero. Very preferably, the Hammett constant of theelectron-withdrawing substituent is not less than 0.2, more preferablynot less than 0.4 and most preferably not less than 0.55. Furtherdetails regarding the definition and determination of the Hammettconstant are well known to the person skilled in the art from the basicsof organic chemistry and are disclosed in standard textbooks. TheHammett constant and the determination thereof for the purposes of thepresent invention are as defined in chapter 9 of Jerry March, AdvancedOrganic Chemistry, John r: Wiley & Sons, Fourth Edition, 1992.

Examples of suitable aromatic or heteroaromatic ring systems having oneor more electron-withdrawing substituents are selected from the groupconsisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl,especially branched terphenyl, quaterphenyl, especially branchedquaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl,imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1- or2-naphthyl, anthracenyl, each of which may be substituted by one or moreR² radicals, particular preference being given to spirobifluorene,fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene,triphenylene groups. Of the groups mentioned, phenyl radicals having oneor more electron-withdrawing substituents are especially preferred.

The preferred electron-withdrawing substituents include F, fluorinatedalkyl groups, CF₃, C_(n)F_(2n+1), C(═O)OR¹, C(═O)N(R¹)₂, B(OR¹)₂, NO₂,CHO, C(═O)R¹, P(═O)(R¹)₂, S(═O)R¹, S(═O)₂R¹ and/or CN, preference beinggiven to CF₃, C_(n)F_(2n+1), C(═O)OR¹, C(═O)N(R¹)₂, NO₂, CHO, C(═O)R¹,S(═O)R¹, S(═O)₂R¹ and/or CN, and particular preference to CN, F,fluorinated alkyl groups, CF₃, C_(n)F_(2n+1). The electron-withdrawingQ¹ group may preferably have two or more electron-withdrawingsubstituents, where these may be the same or different.

Preferably, the symbol Ar^(a) and/or Ar^(b) represents an aryl orheteroaryl radical, such that an aromatic or heteroaromatic group of anaromatic or heteroaromatic ring system is bonded directly to therespective atom of the further group, i.e. via an atom of the aromaticor heteroaromatic group.

In a further preferred embodiment of the invention, the symbol Ar^(a)and/or Ar^(b) is the same or different and is an aromatic orheteroaromatic ring system having 6 to 24 aromatic ring atoms,preferably 6 to 18 aromatic ring atoms, and is more preferably anaromatic ring system having 6 to 12 aromatic ring atoms or aheteroaromatic ring system which has 6 to 13 aromatic ring atoms and maybe substituted in each case by one or more R¹ radicals, but ispreferably unsubstituted, where R¹ may have the definition given above,especially in formula (I).

Advantageously, each symbol Ar^(a) and/or Ar^(b) in formula (I)independently represents an aromatic ring system which has 6 to 12aromatic ring atoms and may be substituted by one or more R¹ radicals,but is preferably unsubstituted, where R¹ may have the definitiondetailed above, especially for formula (I). Especially preferably, eachof Ar^(a) and/or Ar^(b) in formula (I) represents a phenyl ring whichmay be substituted by one or more R¹ radicals, but is preferablyunsubstituted.

Especially preferably, the Ar^(a) and/or Ar^(b) group in formula (I) isdifferent from a donor group as per symbol HL. It may additionally bethe case that the Ar^(a) group in formula (I) is different from a donorgroup as per symbol HL. It may further be the case that the Ar^(b) groupin formula (I) is different from a donor group as per symbol HL.Particularly preferably, both the Ar^(a) and the Ar^(b) groups informula (I) are different from a donor group as per symbol HL.

Especially preferably, the Ar^(a) and/or Ar^(b) group in formula (I) isdifferent from an acceptor group as per symbol Q. It may additionally bethe case that the Ar^(a) group in formula (I) is different from anacceptor group as per symbol Q. It may further be the case that theAr^(b) group in formula (I) is different from an acceptor group as persymbol Q. Particularly preferably, both the Ar^(a) and the Ar^(b) groupsin formula (I) are different from an acceptor group as per symbol Q.

Preferably, the R^(a), R^(b) substituents in formula (I) are selectedfrom the group consisting of F, CN, N(Ar¹)₂, C(═O)Ar¹, P(═O)(Ar¹)₂, astraight-chain alkyl or alkoxy group having 1 to 10 carbon atoms or abranched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms oran alkenyl group having 2 to 10 carbon atoms, each of which may besubstituted by one or more R² radicals, where one or more nonadjacentCH₂ groups may be replaced by O and where one or more hydrogen atoms maybe replaced by D or F, an aromatic or heteroaromatic ring system whichhas 5 to 40 aromatic ring atoms and may be substituted in each case byone or more R² radicals, but is preferably unsubstituted, or an aralkylor heteroaralkyl group which has 5 to 25 aromatic ring atoms and may besubstituted by one or more R² radicals; at the same time, it isoptionally possible for two R¹ substituents bonded to the same carbonatom or to adjacent carbon atoms to form a monocyclic or polycyclic,aliphatic, aromatic or heteroaromatic ring system which may besubstituted by one or more R¹ radicals; where Ar¹ may have thedefinition set out for formula (H-1) to (H-26) or/and formula (Q-26),(Q-27), (Q-28), (Q-29) or (Q-30), where the preferences set out here areapplicable in this definition too. Preferably, Ar¹ is the same ordifferent at each instance and represents an aryl or heteroaryl groupwhich has 5 to 24 and preferably 5 to 12 aromatic ring atoms, and whichmay be substituted in each case by one or more R² radicals, but ispreferably unsubstituted.

Preferably, the symbol R^(a) and/or R^(b) represents an aryl orheteroaryl radical, such that an aromatic or heteroaromatic group of anaromatic or heteroaromatic ring system is bonded directly to therespective atom of the further group, i.e. via an atom of the aromaticor heteroaromatic group.

In a further preferred embodiment of the invention, the symbol R^(a)and/or R^(b) is in each case independently an aromatic or heteroaromaticring system having 5 to 24 aromatic ring atoms, preferably 6 to 18aromatic ring atoms, and is more preferably an aromatic ring systemhaving 6 to 12 aromatic ring atoms or a heteroaromatic ring system whichhas 5 to 13 aromatic ring atoms and may be substituted in each case byone or more R¹ radicals, but is preferably unsubstituted, where R¹ mayhave the definition given above, especially in formula (I).

Advantageously, each symbol R^(a) and/or R^(b) in formula (I)independently represents an aromatic ring system which has 6 to 12aromatic ring atoms and may be substituted by one or more R¹ radicals,but is preferably unsubstituted, where R¹ may have the definitiondetailed above, especially for formula (I). Especially preferably, eachof Ar^(a) and/or Ar^(b) in formula (I) represents a phenyl ring whichmay be substituted by one or more R¹ radicals, but is preferablyunsubstituted.

Especially preferably, the R^(a) and/or R^(b) group in formula (I) isdifferent from a donor group as per symbol HL. It may additionally bethe case that the R^(a) group in formula (I) is different from a donorgroup as per symbol HL. It may further be the case that the R^(b) groupin formula (I) is different from a donor group as per symbol HL.Particularly preferably, both the R^(a) and the R^(b) groups in formula(I) are different from a donor group as per symbol HL.

Especially preferably, the R^(a) and/or R^(b) group in formula (I) isdifferent from an acceptor group as per symbol Q. It may additionally bethe case that the R^(a) group in formula (I) is different from anacceptor group as per symbol Q. It may further be the case that theR^(b) group in formula (I) is different from an acceptor group as persymbol Q. Particularly preferably, both the R^(a) and the R^(b) groupsin formula (I) are different from an acceptor group as per symbol Q.

More preferably, the symbols Ar^(a), Ar^(b), R^(a) and R^(b) in formula(I) are each independently an aromatic or heteroaromatic ring systemhaving preferably 5 to 24 aromatic ring atoms, more preferably having 6to 18 aromatic ring atoms, each of which may be substituted by one ormore R¹ radicals, but is preferably unsubstituted. More preferably, thesymbols Ar^(a), Ar^(b), R^(a) and R^(b) in formula (I) are eachindependently an aromatic ring system having 6 to 12 aromatic ring atomsor a heteroaromatic ring system having 5 to 13 heteroaromatic ringatoms, each of which may be substituted by one or more R¹ radicals, butis preferably unsubstituted, where R¹ may have the definition detailedabove, especially in formula (I). Especially preferably, symbols Ar^(a),Ar^(b), R^(a) and R^(b) in formula (I) each represent a phenyl ringwhich may be substituted by one or more R¹ radicals, but is preferablyunsubstituted.

It is possible here for two or more of the symbols Ar^(a), Ar^(b), R^(a)and/or R^(b) in formula (I) to be joined by a ring closure, where thejoining can more preferably be effected by a bond between the respectiveAr^(a), Ar^(b), R^(a) and/or R^(b) groups in formula (I).

When X is CR¹ or when the aromatic and/or heteroaromatic groups aresubstituted by R¹ substituents, these R¹ substituents are preferablyselected from the group consisting of H, D, F, CN, N(Ar¹)₂, C(═O)Ar¹,P(═O)(Ar¹)₂, a straight-chain alkyl or alkoxy group having 1 to 10carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, each ofwhich may be substituted by one or more R² radicals, where one or morenonadjacent CH₂ groups may be replaced by O and where one or morehydrogen atoms may be replaced by D or F, an aromatic or heteroaromaticring system which has 5 to 24 aromatic ring atoms and may be substitutedin each case by one or more R² radicals, but is preferablyunsubstituted, or an aralkyl or heteroaralkyl group which has 5 to 25aromatic ring atoms and may be substituted by one or more R² radicals;at the same time, it is optionally possible for two R¹ substituentsbonded to the same carbon atom or to adjacent carbon atoms to form amonocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ringsystem which may be substituted by one or more R¹ radicals; where Ar¹may have the definition set out for formula (H-1) to (H-26) or/andformula (Q-26), (Q-27), (Q-28), (Q-29) or (Q-30), where the preferencesset out here are applicable in this definition too.

More preferably, these R¹ substituents are selected from the groupconsisting of H, D, F, CN, N(Ar¹)₂, a straight-chain alkyl group having1 to 8 carbon atoms, preferably having 1, 2, 3 or 4 carbon atoms, or abranched or cyclic alkyl group having 3 to 8 carbon atoms, preferablyhaving 3 or 4 carbon atoms, or an alkenyl group having 2 to 8 carbonatoms, preferably having 2, 3 or 4 carbon atoms, each of which may besubstituted by one or more R² radicals, but is preferably unsubstituted,or an aromatic or heteroaromatic ring system which has 6 to 24 aromaticring atoms, preferably 6 to 18 aromatic ring atoms, more preferably 6 to13 aromatic ring atoms, and may be substituted in each case by one ormore nonaromatic R¹ radicals, but is preferably unsubstituted; at thesame time, it is optionally possible for two R¹ substituents bonded tothe same carbon atom or to adjacent carbon atoms to form a monocyclic orpolycyclic aliphatic ring system which may be substituted by one or moreR² radicals, but is preferably unsubstituted, where Ar¹ may have thedefinition set out above.

Most preferably, the R¹ substituents are selected from the groupconsisting of H and an aromatic or heteroaromatic ring system which has6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring atoms, andmay be substituted in each case by one or more nonaromatic R² radicals,but is preferably unsubstituted.

Preferably, the R¹ radicals do not form a fused ring system with thering atoms of the aryl group or of the heteroaryl group to which the R¹radicals are bonded. This includes the formation of a fused ring systemwith possible R², R³ substituents which may be bonded to the R¹radicals.

It may preferably be the case that the Ar^(a), Ar^(b), Ar¹, Ar², Ar³,Ar⁴, R^(a), R^(b) and/or R¹ group in the structures of formula (I),(H-1) to (H-26), (LAr-1), (LAr-2) and/or (Q-1) to (Q-44) is selectedfrom the group consisting of phenyl, ortho-, meta- or para-biphenyl,terphenyl, especially branched terphenyl, quaterphenyl, especiallybranched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl,imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3- or4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl,phenanthrenyl and/or triphenylenyl, each of which may be substituted byone or more R² radicals, but are preferably unsubstituted, particularpreference being given to phenyl, spirobifluorene, fluorene,dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylenegroups.

It may further be the case that, in a structure of formula (I), (H-1) to(H-26), (LAr-1), (LAr-2) and/or (Q-1) to (Q-44), at least one Ar^(a),Ar^(b), Ar¹, Ar³, Ar⁴, R^(a), R^(b) and/or R¹ radical comprises a groupand is preferably a group selected from the formulae (R¹-1) to (R¹-86):

where the symbols used are as follows:

-   -   Y is O, S or NR², preferably O or S;    -   i at each instance is independently 0, 1 or 2;    -   j at each instance is independently 0, 1, 2 or 3;    -   h at each instance is independently 0, 1, 2, 3 or 4;    -   g at each instance is independently 0, 1, 2, 3, 4 or 5;    -   R² may have the definition given above, especially for formula        (I), and the dotted bond marks the attachment position.        Preference is given here to the groups of the formulae R1-1 to        R1-54 and particular preference to groups of the formulae R1-1,        R1-3, R1-5, R1-6, R1-15, R1-29, R1-34, R1-35, R1-45, R1-46,        R1-47 and/or R1-48.

It may preferably be the case that the sum total of the indices i, j, hand g in the structures of the formula (R¹-1) to (R¹-86) is not morethan 3 in each case, preferably not more than 2 and more preferably notmore than 1.

Preferably, the R² radicals in the formulae (R¹-1) to (R¹-86) do notform a fused aromatic or heteroaromatic ring system, and preferably donot form any fused ring system, with the ring atoms of the aryl group orheteroaryl group to which the R² radicals are bonded. This includes theformation of a fused ring system with possible R³ substituents which maybe bonded to the R² radicals.

Preferably, the L¹ group may form through-conjugation with the Q¹ groupand the aromatic radical to which the L¹ group of formula (I) or (QL) isbonded. Through-conjugation of the aromatic or heteroaromatic systems isformed as soon as direct bonds are formed between adjacent aromatic orheteroaromatic rings. A further bond between the aforementionedconjugated groups, for example via a sulfur, nitrogen or oxygen atom ora carbonyl group, is not detrimental to conjugation. In the case of afluorene system, the two aromatic rings are bonded directly, where thesp³-hybridized carbon atom in position 9 does prevent fusion of theserings, but conjugation is possible since this sp³-hybridized carbon atomin position 9 does not necessarily lie between the Q¹ group and thearomatic radical to which the L¹ group of formula (I) or (QL) is bonded.In contrast, in the case of a second spirobifluorene structure,through-conjugation can be formed if the bond between the Q¹ group andthe aromatic radical of the formula (I) is via the same phenyl group inthe spirobifluorene structure or via phenyl groups in thespirobifluorene structure that are bonded directly to one another andare in one plane. If the bond between the Q¹ group and the aromaticradical of the formula (I) is via different phenyl groups in the secondspirobifluorene structure bonded via the sp³-hybridized carbon atom inposition 9, the conjugation is interrupted. Preferably, the Ar²radicals, for example in formulae (H-1) to (H-26), also formthrough-conjugation with the groups to which the Ar² radicals arebonded. In addition, the connecting structures of the formula (LAr-1)and/or (LAr-2) form through-conjugation with the groups to which theconnecting structures of the formula (LAr-1) and/or (LAr-2) are bonded.

In a further preferred embodiment of the invention, L¹ or the Ar² groupis an aromatic or heteroaromatic ring system which has 5 to 14 aromaticor heteroaromatic ring atoms, preferably an aromatic ring system whichhas 6 to 12 carbon atoms, and which may be substituted by one or more R¹radicals, but is preferably unsubstituted, where R¹ may have thedefinition given above, especially for formula (I). More preferably, L¹or the Ar² group is an aromatic ring system having 6 to 10 aromatic ringatoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ringatoms, each of which may be substituted by one or more R² radicals, butis preferably unsubstituted, where R² may have the definition givenabove, especially for formula (I).

Further preferably, the symbol L¹ or the Ar² group detailed in theformulae (H-1) to (H-26) that are detailed in the structures of formula(QL) inter alia is the same or different at each instance and is a bondor an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6to 13 ring atoms, more preferably 6 to 10 ring atoms, such that anaromatic or heteroaromatic group of an aromatic or heteroaromatic ringsystem is bonded directly, i.e. via an atom of the aromatic orheteroaromatic group, r: to the respective atom of the further group.

It may additionally be the case that the symbol L¹ detailed in thestructures of formula (QL) inter alia or the Ar² group detailed in theformulae (H-1) to (H-26) comprises an aromatic ring system having notmore than two fused aromatic and/or heteroaromatic rings, preferably nothaving any fused aromatic or heteroaromatic ring system. Accordingly,naphthyl structures are preferred over anthracene structures. Inaddition, fluorenyl, spirobifluorenyl, dibenzofuranyl and/ordibenzothienyl structures are preferred over naphthyl structures.

Particular preference is given to structures having no fusion, forexample phenyl, biphenyl, terphenyl and/or quaterphenyl structures.

Examples of suitable aromatic or heteroaromatic ring systems L¹ or Ar²are selected from the group consisting of phenyl, ortho-, meta- orpara-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl,especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3-or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl,imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3- or4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl,phenanthrenyl and/or triphenylenyl, each of which may be substituted byone or more R² radicals, but are preferably unsubstituted, particularpreference being given to phenyl, spirobifluorene, fluorene,dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylenegroups.

It may further be the case that the Ar² group in the structure offormulae (H-1) to (H-26) and/or the L¹ group in formula (QL) is a bondor a group selected from the formulae (L¹-1) to (L¹-108) or thestructure of the formula (LAr-1) or (LAr-2) represents a bond or forms agroup selected from the formulae (L¹-1) to (L¹-108)

where the dotted bonds in each case mark the attachment positions, theindex k at each instance is independently 0 or 1, the index l at eachinstance is independently 0, 1 or 2, the index j at each instance isindependently 0, 1, 2 or 3; the index h at each instance isindependently 0, 1, 2, 3 or 4, the index g at each instance isindependently is 0, 1, 2, 3, 4 or 5; the symbol Y is O, S or NR²,preferably O or S; and the symbol R² has the definition given above,especially for formula (I).

It may preferably be the case that the sum total of the indices k, l, g,h and j in the structures of the formula (L¹-1) to (L¹-108) is at most 3in each case, preferably at most 2 and more preferably at most 1.

Preferred compounds according to the invention comprise an L¹ or Ar²group which represents a bond or which is selected from one of theformulae (L¹-1) to (L¹-78) and/or (L¹-92) to (L¹-108), preferably of theformula (L¹-1) to (L¹-54) and/or (L¹-92) to (L¹-108), especiallypreferably of the formula (L¹-1) to (L¹-29) and/or (L¹-92) to (L¹-103).Advantageously, the sum total of the indices k, l, g, h and j in thestructures of the formulae (L¹-1) to (L¹-78) and/or (L¹-92) to (L¹-108),preferably of the formula (L¹-1) to (L¹-54) and/or (L¹-92) to (L¹-108),especially preferably of the formula (L¹-1) to (L¹-29) and/or (L¹-92) to(L¹-103), may in each case be not more than 3, preferably not more than2 and more preferably not more than 1.

Preferably, the R² radicals in the formulae (L¹-1) to (L¹-108) do notform a fused aromatic or heteroaromatic ring system, and preferably donot form any fused ring system, with the ring atoms of the aryl group orheteroaryl group to which the R² radicals are bonded. This includes theformation of a fused ring system with possible R³ substituents which maybe bonded to the R² radicals.

In a further preferred embodiment of the invention, R², for example in astructure of formula (I) and preferred embodiments of this structure orthe structures where reference is made to these formulae, is the same ordifferent at each instance and is selected from the group consisting ofH, D, an aliphatic hydrocarbyl radical having 1 to 10 carbon atoms,preferably having 1, 2, 3 or 4 carbon atoms, or an aromatic orheteroaromatic ring system which has 5 to 30 aromatic ring atoms,preferably 5 to 24 aromatic ring atoms, more preferably 5 to 13 aromaticring atoms, and may be substituted by one or more alkyl groups eachhaving 1 to 4 carbon atoms, but is preferably unsubstituted.

In a further preferred embodiment of the invention, R³, for example in astructure of formula (I) and preferred embodiments of this structure orthe structures where reference is made to these formulae, is the same ordifferent at each instance and is selected from the group consisting ofH, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 10 carbonatoms, preferably having 1, 2, 3 or 4 carbon atoms, or an aromatic orheteroaromatic ring system which has 5 to 30 aromatic ring atoms,preferably 5 to 24 aromatic ring atoms, more preferably 5 to 13 aromaticring atoms, and may be substituted by one or more alkyl groups eachhaving 1 to 4 carbon atoms, but is preferably unsubstituted.

When the compound of the invention is substituted by aromatic orheteroaromatic R¹ or R² groups, it is preferable when these do not haveany aryl or heteroaryl groups having more than two aromatic six-memberedrings fused directly to one another. More preferably, the substituentsdo not have any aryl or heteroaryl groups having six-membered ringsfused directly to one another at all. The reason for this preference isthe low triplet energy of such structures. Fused aryl groups which havemore than two aromatic six-membered rings fused directly to one anotherbut are nevertheless also suitable in accordance with the invention arephenanthrene and triphenylene, since these also have a high tripletlevel.

Particular preference is given to compounds of the invention having thefollowing properties:

Ar^(a) R^(a) Acceptor group (QL) and Ar^(b) and R^(b) Q¹ L¹ Donor groupR¹-1 to R¹-1 to Q-1 to Q-44 bond H-1 to H-44 R¹-86 R¹-86 R¹-1 to R¹-1 toQ-1 to Q-44 bond H-1 to H-44 R¹-82 R¹-82 R¹-1 to R¹-1 to Q-1 to Q-44bond H-1 to H-44 R¹-54 R¹-54 R¹-1 R¹-1 Q-1 to Q-44 bond H-1 to H-44 R¹-1to R¹-1 to Q-1 to Q-44 L-1 H-1 to H-44 R¹-86 R¹-86 R¹-1 to R¹-1 to Q-1to Q-44 L-1 H-1 to H-44 R¹-82 R¹-82 R¹-1 to R¹-1 to Q-1 to Q-44 L-1 H-1to H-44 R¹-54 R¹-54 R¹-1 R¹-1 Q-1 to Q-44 L-1 H-1 to H-44

Particular preference is given to compounds of the invention comprisingat least one donor group of formulae (H-1) to (H-26) where the Ar² groupis a connecting structure of the formula (LAr-1), and at least oneacceptor group of formula (QL) where L¹ can be represented by aconnecting structure of the formula (LAr-2), where the followingadditional properties are fulfilled:

Index s in Index t in formula formula Ar^(a) and Ar^(b) R^(a) and R^(b)(LAr-1) (LAr-2) R¹-1 to R¹-86 R¹-1 to R¹-86 0, 1 or 2 0 R¹-1 to R¹-86R¹-1 to R¹-86 0, 1 or 2 1 R¹-1 to R¹-86 R¹-1 to R¹-86 0, 1 or 2 2 R¹-1to R¹-86 R¹-1 to R¹-86 0 0, 1 or 2 R¹-1 to R¹-86 R¹-1 to R¹-86 1 0, 1 or2 R¹-1 to R¹-86 R¹-1 to R¹-86 2 0, 1 or 2 R¹-1 to R¹-82 R¹-1 to R¹-82 00 R¹-1 to R¹-82 R¹-1 to R¹-82 1 1 R¹-1 to R¹-82 R¹-1 to R¹-82 2 2 R¹-1to R¹-82 R¹-1 to R¹-82 0 1 R¹-1 to R¹-82 R¹-1 to R¹-82 1 2 R¹-1 to R¹-82R¹-1 to R¹-82 2 3 R¹-1 to R¹-82 R¹-1 to R¹-82 1 0 R¹-1 to R¹-82 R¹-1 toR¹-82 2 2 R¹-1 to R¹-82 R¹-1 to R¹-82 3 2 R¹-1 R¹-1 0, 1 or 2 0 R¹-1R¹-1 0, 1 or 2 1 R¹-1 R¹-1 0, 1 or 2 2 R¹-1 R¹-1 0 0, 1 or 2 R¹-1 R¹-1 10, 1 or 2 R¹-1 R¹-1 2 0, 1 or 2 R¹-1 R¹-1 0 0 R¹-1 R¹-1 1 1 R¹-1 R¹-1 22 R¹-1 R¹-1 0 1 R¹-1 R¹-1 1 2 R¹-1 R¹-1 2 3 R¹-1 R¹-1 1 0 R¹-1 R¹-1 2 1R¹-1 R¹-1 3 2

In the tables set out above, the assignment that Ar^(a) and Ar^(b) isR¹-1 to R¹-86 means that both the Ar^(a) group and the Ar^(b) group isselected from the radicals of the above-detailed formulae R¹-1 to R¹-86,preferably R¹-1. The assignment of R^(a) and R^(b) means that both theR^(a) group and the R^(b) group are selected from the radicals of theabove-detailed formulae R¹-1 to R¹-86, preferably R¹-1. The furtherassignments apply correspondingly.

Examples of suitable compounds of the invention are the structures ofthe following formulae 1 to 51 shown below:

Preferred embodiments of compounds of the invention are recitedspecifically in the examples, these compounds being usable alone or incombination with further compounds for all purposes of the invention.

Provided that the conditions specified in Claim 1 are complied with, theabovementioned preferred embodiments can be combined with one another asdesired. In a particularly preferred embodiment of the invention, theabovementioned preferred embodiments apply simultaneously.

The compounds of the invention are preparable in principle by variousprocesses. However, the processes described hereinafter have been foundto be particularly suitable.

Therefore, the present invention further provides a process forpreparing the compounds comprising at least one structure of formula(I), in which a compound comprising at least one donor group is joinedto an acceptor group in a coupling reaction.

Suitable compounds having a donor group are in many cases commerciallyavailable, and the starting compounds detailed in the examples areobtainable by known processes, and so reference is made thereto.

Preferably, a cyclopentadienone derivative can be reacted with an alkynederivative, which can be effected in a Diels-Alder reaction. TheDiels-Alder product then reacts with elimination of CO to give acompound of the invention. This reaction is advantageous especially ifthe Ar^(a), Ar^(b), R^(a) and R^(b) groups represent aryl or heteroarylgroups.

It is possible here to obtain corresponding alkyne derivatives ofcompounds that preferably comprise a donor group and/or an acceptorgroup by reaction of compounds containing corresponding reactive groupswith aromatic or heteroaromatic alkyne compounds. Coupling reactionssuitable for this purpose, for example Suzuki coupling, are commonknowledge, and the reaction known as the Sonogashira reaction has beenfound to be particularly useful for this purpose. The reactionconditions for a Suzuki coupling or a Sonogashira reaction are widelyknown in the technical field, and the examples give valuable pointers inthis connection.

The reactive reactant compounds for use as reactant for a Suzukicoupling or a Sonogashira reaction can be obtained, for example, byknown halogenations, preferably brominations, from known aryl orheteroaryl compounds.

These compounds can be reacted with further aryl compounds by knowncoupling reactions, the necessary conditions for this purpose beingknown to the person skilled in the art, and detailed specifications inthe examples give support to the person skilled in the art in conductingthese reactions.

Particularly suitable and preferred coupling reactions which all lead toC—C bond formation and/or C—N bond formation are those according toBUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA andHIYAMA. These reactions are widely known, and the examples will providethe person skilled in the art with further pointers.

It is possible by these processes, if necessary followed bypurification, for example recrystallization or sublimation, to obtainthe compounds of the invention comprising structures of formula (I) inhigh purity, preferably more than 99% (determined by means of ¹H NMRand/or HPLC).

The compounds of the invention may also have suitable substituents, forexample relatively long alkyl groups (about 4 to 20 carbon atoms),especially branched alkyl groups, or optionally substituted aryl groups,for example xylyl, mesityl or branched terphenyl or quaterphenyl groups,which bring about solubility in standard organic solvents, for exampletoluene or xylene, at room temperature in a sufficient concentration, inorder to be able to process the compounds from solution. These solublecompounds are of particularly good suitability for processing fromsolution, for example by printing methods. In addition, it should beemphasized that the compounds of the invention comprising at least onestructure of the formula (I) already have enhanced solubility in thesesolvents.

The compounds of the invention may also be mixed with a polymer. It islikewise possible to incorporate these compounds covalently into apolymer. This is especially possible with compounds substituted byreactive leaving groups such as bromine, iodine, chlorine, boronic acidor boronic ester, or by reactive polymerizable groups such as olefins oroxetanes. These may find use as monomers for production of correspondingoligomers, dendrimers or polymers. The oligomerization or polymerizationis preferably effected via the halogen functionality or the boronic acidfunctionality or via the polymerizable group. It is additionallypossible to crosslink the polymers via groups of this kind. Thecompounds and polymers of the invention may be used in the form of acrosslinked or uncrosslinked layer.

The invention therefore further provides oligomers, polymers ordendrimers containing one or more of the above-detailed structures ofthe formula (I) or compounds of the invention, wherein one or more bondsof the compounds of the invention or of the structures of the formula(I) to the polymer, oligomer or dendrimer are present. According to thelinkage of the structures of the formula (I) or of the compounds, thesetherefore form a side chain of the oligomer or polymer or are bondedwithin the main chain. The polymers, oligomers or dendrimers may beconjugated, partly conjugated or nonconjugated. The oligomers orpolymers may be linear, branched or dendritic. For the repeat units ofthe compounds of the invention in oligomers, dendrimers and polymers,the same preferences apply as described above.

For preparation of the oligomers or polymers, the monomers of theinvention are homopolymerized or copolymerized with further monomers.Preference is given to copolymers wherein the units of formula (I) orthe preferred embodiments recited above and hereinafter are present toan extent of 0.01 to 99.9 mol %, preferably 5 to 90 mol %, morepreferably 20 to 80 mol %. Suitable and preferred comonomers which formthe polymer base skeleton are chosen from fluorenes (for exampleaccording to EP 842208 or WO 2000/022026), spirobifluorenes (for exampleaccording to EP 707020, EP 894107 or WO 2006/061181), paraphenylenes(for example according to WO 92/18552), carbazoles (for exampleaccording to WO 2004/070772 or WO 2004/113468), thiophenes (for exampleaccording to EP 1028136), dihydrophenanthrenes (for example according toWO 2005/014689), cis- and trans-indenofluorenes (for example accordingto WO 2004/041901 or WO 2004/113412), ketones (for example according toWO 2005/040302), phenanthrenes (for example according to WO 2005/104264or WO 2007/017066) or else a plurality of these units. The polymers,oligomers and dendrimers may contain still further units, for examplehole transport units, especially those based on triarylamines, and/orelectron transport units.

Additionally of particular interest are compounds of the invention whichfeature a high glass transition temperature. In this connection,preference is given especially to compounds of the invention comprisingstructures of the general formula (I) or the preferred embodimentsrecited above and hereinafter which have a glass transition temperatureof at least 70° C., more preferably of at least 110° C., even morepreferably of at least 125° C. and especially preferably of at least150° C., determined in accordance with DIN 51005 (2005-08 version).

For the processing of the compounds of the invention from a liquidphase, for example by spin-coating or by printing methods, formulationsof the compounds of the invention are required. These formulations may,for example, be solutions, dispersions or emulsions. For this purpose,it may be preferable to use mixtures of two or more solvents. Suitableand preferred solvents are, for example, toluene, anisole, o-, m- orp-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF,methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially3-phenoxytoluene, (−)-fenchone, 1,2,3,5-tetramethylbenzene,1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole,2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole,3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol,benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone,cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane,methyl benzoate, NMP, p-cymene, phenetole, 1,4-diisopropylbenzene,dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycolbutyl methyl ether, diethylene glycol dibutyl ether, triethylene glycoldimethyl ether, diethylene glycol monobutyl ether, tripropylene glycoldimethyl ether, tetraethylene glycol dimethyl ether,2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene,octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, hexamethylindane ormixtures of these solvents.

The present invention therefore further provides a formulationcomprising a compound of the invention and at least one furthercompound. The further compound may, for example, be a solvent,especially one of the abovementioned solvents or a mixture of thesesolvents. The further compound may alternatively be at least one furtherorganic or inorganic compound which is likewise used in the electronicdevice, for example an emitting compound, especially a phosphorescentdopant, and/or a further matrix material. This further compound may alsobe polymeric.

The present invention therefore still further provides a compositioncomprising a compound of the invention and at least one furtherorganically functional material. Functional materials are generally theorganic or inorganic materials introduced between the anode and cathode.Preferably, the organically functional material is selected from thegroup consisting of fluorescent emitters, phosphorescent emitters, hostmaterials, electron transport materials, electron injection materials,hole conductor materials, hole injection materials, electron blockermaterials, hole blocker materials, wide band gap materials andn-dopants.

The present invention therefore also relates to a composition comprisingat least one compound comprising structures of formula (I) or thepreferred embodiments recited above and hereinafter and at least onematrix material. The matrix material is also referred to as hostmaterial. In this context, the compound of the invention may haveproperties of a matrix material or of an emitter. If the compoundcomprising structures of formula (I) or the preferred embodimentsrecited above and hereinafter is used as matrix material, a hostmaterial other than the compounds of the invention will especially alsobe used herein as further matrix material. According to a particularaspect of the present invention, the further matrix material hashole-transporting properties.

The matrix material may especially be selected according to the natureof the electronic device, especially of the use of the compound of theinvention. If the compound of the invention is used, for example, asemitter, for example in organic electroluminescent devices or organiclight-emitting electrochemical cells, the host material preferably has agreater energy gap than the compound comprising structures of formula(I) which is used in accordance with the invention as fluorescent TADFmaterial.

Preferably, the host material acts as electron or hole conductor or as acombined electron/hole conductor.

In one embodiment, the absorption spectrum of the compound of theinvention used as fluorescent TADF material overlaps with thephotoluminescence spectrum of the at least one host material, such thatan energy transition is possible between the compound of the inventionand the at least one host material. In principle, it is possible to usehost materials as known or customary for employment in OLECs or OLEDs.

In one embodiment, the host material is a hole- or electron-transportingmaterial.

In one embodiment, the host material has a lowest triplet state T₁ ^(H)having an energy higher than the energy of the lowest triplet state T₁of the uncharged organic luminescent compound.

Suitable host materials are selected, for example, from anthracenes,benzanthracenes, indenofluorenes, fluorenes, spiro-bifluorenes,phenanthrenes, dehydrophenanthrenes, dehydrofluorenes, thiophenes,triazines, carbazoles, indenocarbazoles, indolocarbazoles, pyrimidines,lactams, benzophenones, triarylamines, quinazolines and imidazoles.

Very preferred host materials are selected from indenofluorenes,fluorenes, spiro-bifluorenes, phenanthrenes, dehydrophenanthrenes,dehydrofluorenes, thiophenes, triazines, carbazoles, indenocarbazoles,indolocarbazoles, pyrimidines, lactams, benzophenones, triarylamines,quinazolines and imidazoles.

In one embodiment the composition comprises four or fewer hostmaterials, in a further embodiment three or fewer host materials, and ina further embodiment one or two host materials.

Particularly preferred host materials are selected from the group of theoligoarylenes, for example 2,2′,7,7′-tetraphenylspirobifluorene which isdescribed in EP 676461, or dinaphthylanthracene. Preference is given tooligoarylenes comprising fused aromatic groups, for examplephenanthrene, tetracene, coronene, chrysene, fluorene, spirofluorene,perylene, phthaloperylene, naphthaloperylene, decacyclene, rubrene,oligoarylenevinylenes, for example4,4′-bis(2,2-diphenylethenyl)-1,1′-biphenyl (DPVBi) or4,4-bis-2,2-diphenylvinyl-1,1-spirobiphenyl (spiro-DPVBi), as describedin EP 676461.

Further suitable host materials are polypodal metal complexes asdescribed, for example, in WO 2004/081017, for example metal complexeswith 8-hydroxyquinoline, such as aluminium(III) tris(8-hydroxyquinoline)(Alq₃), orbis-(2-methyl-8-quinolinolato)-4-(phenylphenolinolato)aluminium,imidazole chelate compounds as described in US 2007/0092753 A1, and alsoquinoline-metal complexes, aminoquinoline-metal complexes,benzoquinoline-metal complexes, hole-transporting materials asdescribed, for example, in WO 2004/058911, electron-transportingmaterials, especially ketones, phosphine oxides, sulfoxides asdescribed, for example, in WO 2005/084081 and WO 2005/08408,atropisomers as described in WO 2006/048268, boronic acid derivatives asdescribed, for example, in WO 2006/117052, or benzanthracenes asdescribed in DE 102007024850.

Further suitable host materials are oligoarylenes such as naphthalene,anthracene, benzanthracene and pyrene, and also atropisomers of thesecompounds, ketones, phosphine oxides and sulfoxides. Preferably, thehost material is selected from the class of the oligoarylenes,especially naphthalene, anthracene, benzanthracene and pyrene. Anoligoaryl compound in the context of this invention is understood tomean a compound comprising at least three aryl or arylene groups joinedto one another.

Further suitable host materials are selected from compounds of theformula (HM-1):

Ar⁵-(Ar⁶)_(p)-Ar⁷  Formula (HM-1)

-   -   where:    -   Ar⁵, Ar⁶, Ar⁷ are the same or different at each instance and are        an aryl or heteroaryl group having 5 to 30 aromatic ring atoms,        which may also be mono- or polysubstituted,    -   p=1, 2 or 3;    -   where the sum total of the π electrons in the Ar⁵, Ar⁶, Ar⁷        groups is at least 30 when p=1 and at least 36 if p=2 and at        least 42 if p=3.

Within the host materials of the formula (HM-1), Ar⁶ is preferablyanthracene which may be substituted by one or more R¹ radicals, wherethe Ar⁵ and Ar⁷ groups are bonded at positions 9 and 10 in a furtherembodiment. More preferably, at least one of the Ar⁵ and Ar⁷ groups is afused aryl group which is preferably selected from the group of 1- or2-naphthyl, 2-, 3- or 9-phenanthrenyl or 2-, 3-, 4-, 5-, 6- or7-benzanthracenyl, each of which may be mono- or polysubstituted by R¹.R¹ here is as defined above.

Suitable anthracene compounds are described, for example, in US2007/0092753 A1 and US 2007/0252517 A1, for example2-(4-methylphenyl)-9,10-di(2-naphthyl)anthracene,9-(2-naphthyl)-10-(1,1′-biphenyl)anthracene and9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene,9,10-diphenylanthracene, 9,10-bis(phenylethynyl)anthracene and1,4-bis(9′-ethynylanthracenyl)benzene. Preference is also given to hostmaterials having at least two anthracene groups (US 2008/0193796 A1),for example 10,10′-bis[1,1′,4′, 1″ ]terphenyl-2-yl-9,9′-bisanthracenyl.

Further suitable host materials are derivatives of arylamines,styrylamines, fluorescein, perinone, phthaloperinone, naphthaloperinone,diphenylbutadiene, tetraphenylbutadiene, cyclopentadienes,tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, coumarin,oxadiazole, bisbenzoxazoline, oxazone, pyridine, pyrazine, imines,benzothiazoles, benzoxazoles, benzimidazoles (US 2007/0092753 A1), forexample 2,2′,2″-(1,3,5-phenylene)tris[1-phenyl-1H-benzimidazole],aldazines, stilbenes, styrylarylene derivatives, for example9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, and distyrylarylenederivatives (U.S. Pat. No. 5,121,029), diphenylethylene,vinylanthracene, diaminocarbazole, pyran, thiopyran,diketopyrrolopyrrole, polymethine, merocyanine, acridone, quinacridone,cinnamic esters and fluorescent dyes.

In a preferred embodiment, arylamine and styrylamine derivatives areused as host materials, for example4,4′-bis[N-(1-naphthyl)-N-(2-naphthyl)amino]biphenyl (TNB).

Oligoarylenes suitable as host materials are described, for example, inUS 2003/0027016 A1, U.S. Pat. No. 7,326,371 B2, US 2006/043858 A, U.S.Pat. No. 7,326,371 B2, US 2003/0027016 A1, WO 2007/114358, WO2008/145239, JP 3148176 B2, EP 1009044, US 2004/018383, WO 2005/061656A1, EP 0681019B1, WO 2004/013073A1, U.S. Pat. No. 5,077,142, WO2007/065678, and US 2007/0205412 A1.

Compounds particularly preferred as host material are shown in thefollowing formulae (HM-2) to (HM-8):

Further suitable host materials are spirobifluorene and derivativesthereof, for example spiro-DPVBi which is described in EP 0676461, orindenofluorene which is described in U.S. Pat. No. 6,562,485.

The combination of compounds of the invention which are used as emittersor as TADF material with the aforementioned host materials, in order toform an emitting layer in an OLEC, can be correspondingly supplementedwith an electrolyte which provides mobile ions, as known from the priorart as described particularly in the introductory part of thisapplication.

The present invention further provides a composition comprising at leastone compound comprising at least one structure of formula (I) or thepreferred embodiments recited above and hereinafter and at least onewide band gap material, a wide band gap material being understood tomean a material in the sense of the disclosure of U.S. Pat. No.7,294,849. These systems exhibit exceptional advantageous performancedata in electroluminescent devices.

Preferably, the additional compound may have a band gap of 2.5 eV ormore, preferably 3.0 eV or more, very preferably of 3.5 eV or more. Oneway of calculating the band gap is via the energy levels of the highestoccupied molecular orbital (HOMO) and the lowest unoccupied molecularorbital (LUMO).

Molecular orbitals, especially also the highest occupied molecularorbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), theenergy levels thereof and the energy of the lowest triplet state T₁ andthat of the lowest excited singlet state S₁ of the materials aredetermined via quantum-chemical calculations. For calculation of organicsubstances without metals, an optimization of geometry is firstconducted by the “Ground State/Semi-empirical/Default Spin/AM1/Charge0/Spin Singlet” method. Subsequently, an energy calculation is effectedon the basis of the optimized geometry. This is done using the“TD-SCF/DFT/Default Spin/B3PW91” method with the “6-31G(d)” basis set(charge 0, spin singlet). For metal-containing compounds, the geometryis optimized via the “Ground State/Hartree-Fock/Default Spin/LanL2MB/Charge 0/Spin Singlet” method. The energy calculation is effectedanalogously to the above-described method for the organic substances,except that the “LanL2DZ” basis set is used for the metal atom and the“6-31G(d)” basis set for the ligands. The HOMO energy level HEh or LUMOenergy level LEh is obtained from the energy calculation in Hartreeunits. This is used to determine the HOMO and LUMO energy levels inelectron volts, calibrated by cyclic voltammetry measurements, asfollows:

HOMO(eV)=((HEh*27.212)−0.9899)/1.1206

LUMO(eV)=((LEh*27.212)−2.0041)/1.385

These values are to be regarded as HOMO and LUMO energy levels of thematerials in the context of this application.

The lowest triplet state T₁ is defined as the energy of the tripletstate having the lowest energy, which is apparent from thequantum-chemical calculation described.

The lowest excited singlet state S₁ is defined as the energy of theexcited singlet state having the lowest energy, which is apparent fromthe quantum-chemical calculation described.

The method described herein is independent of the software package usedand always gives the same results. Examples of frequently utilizedprograms for this purpose are “Gaussian09 W” (Gaussian Inc.) and Q-Chem4.1 (Q-Chem, Inc.).

In addition, a compound of the invention can be used as matrix materialin combination with an emitter.

Therefore, the present invention also relates to a compositioncomprising at least one compound having structures of formula (I) or thepreferred embodiments recited above and hereinafter and at least onefluorescent emitter, the term “fluorescent emitters” also beingunderstood to mean fluorescent dopants. It may preferably be the casethat the weight ratio of fluorescent emitter to compound, oligomer,polymer or dendrimer according to the present invention is in the rangefrom 0.1% to 50% by weight, 1% to 20% by weight and 3% to 15% by weight.

The present invention also relates to a composition comprising at leastone compound comprising structures of formula (I) or the preferredembodiments recited above and hereinafter and at least onephosphorescent emitter, the term “phosphorescent emitters” also beingunderstood to mean phosphorescent dopants.

A dopant in a system comprising a matrix material and a dopant isunderstood to mean that component having the smaller proportion in themixture. Correspondingly, a matrix material in a system comprising amatrix material and a dopant is understood to mean that component havingr: the greater proportion in the mixture.

Preferred phosphorescent dopants for use in matrix systems, preferablymixed matrix systems, are the preferred phosphorescent dopants specifiedhereinafter.

The term “phosphorescent dopants” typically encompasses compounds wherethe emission of light is effected through a spin-forbidden transition,for example a transition from an excited triplet state or a state havinga higher spin quantum number, for example a quintet state.

Suitable phosphorescent compounds (=triplet emitters) are especiallycompounds which, when suitably excited, emit light, preferably in thevisible region, and also contain at least one atom of atomic numbergreater than 20, preferably greater than 38 and less than 84, morepreferably greater than 56 and less than 80, especially a metal havingthis atomic number. Preferred phosphorescence emitters used arecompounds containing copper, molybdenum, tungsten, rhenium, ruthenium,osmium, rhodium, iridium, palladium, platinum, silver, gold or europium,especially compounds containing iridium or platinum. In the context ofthe present invention, all luminescent compounds containing theabovementioned metals are regarded as phosphorescent compounds.

Examples of the above-described emitters can be found in applications WO00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/0258742, WO2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO2011/032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO2016/124304, WO 2016/015815, WO 2016/000803, WO 2015/117718, WO2015/104045 and WO 2015/036074. In general, all phosphorescent complexesas used for phosphorescent OLEDs according to the prior art and as knownto those skilled in the art in the field of organic electroluminescenceare suitable, and the person skilled in the art will be able to usefurther phosphorescent complexes without exercising inventive r: skill.

Explicit examples of phosphorescent dopants are adduced in the followingtable:

The above-described compound comprising structures of the formula (I) orthe above-detailed preferred embodiments can preferably be used asactive component in an electronic device. An electronic device isunderstood to mean any device comprising anode, cathode and at least onelayer between anode and cathode, said layer comprising at least oneorganic or organometallic compound. The electronic device of theinvention thus comprises anode, cathode and at least one interveninglayer containing at least one compound comprising structures of theformula (I).

Preferred electronic devices here are selected from the group consistingof organic electroluminescent devices (OLEDs, PLEDs), organic integratedcircuits (O-ICs), organic field-effect transistors (O-FETs), organicthin-film transistors (O-TFTs), organic light-emitting transistors(O-LETs), organic solar cells (O-SCs), organic optical detectors,organic photoreceptors, organic field-quench devices (O-FQDs), organicelectrical sensors, light-emitting electrochemical cells (LECs),preferably organic light-emitting electrochemical cells (OLECs), organiclaser diodes (O-lasers) and organic plasmon emitting devices (D. M.Koller et al., Nature Photonics 2008, 1-4), preferably organicelectroluminescent devices (OLEDs, PLEDs) or organic light-emittingelectrochemical cells (OLECs), especially phosphorescent OLEDs ororganic light-emitting electrochemical cells OLECs, containing at leastone compound comprising structures of the formula (I) in at least onelayer. Particular preference is given to organic electroluminescentdevices. Active components are generally the organic or inorganicmaterials introduced between the anode and cathode, for example chargeinjection, charge transport or charge blocker materials, but especiallyemission materials and matrix materials.

A preferred embodiment of the invention is organic electroluminescentdevices. The organic electroluminescent device comprises cathode, anodeand at least one emitting layer. Apart from these layers, it maycomprise still further layers, for example in each case one or more holeinjection layers, hole transport layers, hole blocker layers, electrontransport layers, electron injection layers, exciton blocker layers,electron blocker layers, charge generation layers and/or organic orinorganic p/n junctions. At the same time, it is possible that one ormore hole transport layers are p-doped, for example with metal oxidessuch as MoO₃ or WO₃ or with (per)fluorinated electron-deficient aromaticsystems, and/or that one or more electron transport layers are n-doped.It is likewise possible for interlayers to be introduced between twoemitting layers, these having, for example, an exciton-blocking functionand/or controlling the charge balance in the electroluminescent device.However, it should be pointed out that not necessarily every one ofthese layers need be present.

In this case, it is possible for the organic electroluminescent deviceto contain an emitting layer, or for it to contain a plurality ofemitting layers. If a plurality of emission layers are present, thesepreferably have several emission maxima between 380 nm and 750 nmoverall, such that the overall result is white emission; in other words,various emitting compounds which may fluoresce or phosphoresce are usedin the emitting layers. Especially preferred are three-layer systemswhere the three layers exhibit blue, green and orange or red emission(for the basic construction see, for example, WO 2005/011013), orsystems having more than three emitting layers. The system may also be ahybrid system wherein one or more layers fluoresce and one or more otherlayers phosphoresce.

In a preferred embodiment of the invention, the organicelectroluminescent device contains the compound of the inventioncomprising structures of formula (I) or the above-detailed preferredembodiments as matrix material, preferably as electron-conducting matrixmaterial, in one or more emitting layers, preferably in combination witha further matrix material, preferably a hole-conducting matrix material.In a further preferred embodiment of the invention, the further matrixmaterial is an electron-transporting compound.

In yet a further preferred embodiment, the further matrix material is acompound having a large band gap which is not involved to a significantdegree, if at all, in the hole and electron transport in the layer. Anemitting layer comprises at least one emitting compound.

Suitable matrix materials which can be used in combination with thecompounds of formula (I) or according to the preferred embodiments arearomatic ketones, aromatic phosphine oxides or aromatic sulfoxides orsulfones, for example according to WO 2004/013080, WO 2004/093207, WO2006/005627 or WO 2010/006680, triarylamines, especially monoamines, forexample according to WO 2014/015935, carbazole derivatives, e.g. CBP(N,N-biscarbazolylbiphenyl) or the carbazole derivatives disclosed in WO2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO2008/086851, indolocarbazole derivatives, for example according to WO2007/063754 or WO 2008/056746, indenocarbazole derivatives, for exampleaccording to WO 2010/136109 and WO 2011/000455, azacarbazolederivatives, for example according to EP 1617710, EP 1617711, EP1731584, JP 2005/347160, bipolar matrix materials, for example accordingto WO 2007/137725, silanes, for example according to WO 2005/111172,azaboroles or boronic esters, for example according to WO 2006/117052,triazine derivatives, for example according to WO 2010/015306, WO2007/063754 or WO 2008/056746, zinc complexes, for example according toEP 652273 or WO 2009/062578, diazasilole or tetraazasilole derivatives,for example according to WO 2010/054729, diazaphosphole derivatives, forexample according to WO 2010/054730, bridged carbazole derivatives, forexample according to US 2009/0136779, WO 2010/050778, WO 2011/042107, WO2011/088877 or WO 2012/143080, triphenylene derivatives, for exampleaccording to WO 2012/048781, lactams, for example according to WO2011/116865, WO 2011/137951 or WO 2013/064206, or 4-spirocarbazolederivatives, for example according to WO 2014/094963 or the as yetunpublished application EP 14002104.9. It is likewise possible for afurther phosphorescent emitter which emits at a shorter wavelength thanthe actual emitter to be present as co-host in the mixture.

Preferred co-host materials are triarylamine derivatives, especiallymonoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives,lactams and carbazole derivatives.

It may also be preferable to use a plurality of different matrixmaterials as a mixture, especially at least one electron-conductingmatrix material and at least one hole-conducting matrix material.Preference is likewise given to the use of a mixture of acharge-transporting matrix material and an electrically inert matrixmaterial having no significant involvement, if any, in the chargetransport, as described, for example, in WO 2010/108579.

It is further preferable to use a mixture of two or more tripletemitters together with a matrix. In this case, the triplet emitterhaving the shorter-wave emission spectrum serves as co-matrix for thetriplet emitter having the longer-wave emission spectrum.

More preferably, it is possible to use a compound of the inventioncomprising structures of formula (I), in a preferred embodiment, asmatrix material in an emission layer of an organic electronic device,especially in an organic electroluminescent device, for example in anOLED or OLEC. In this case, the matrix material containing compoundcomprising structures of formula (I) or the preferred embodimentsrecited above and hereinafter is present in the electronic device incombination with one or more dopants, preferably phosphorescent dopants.

The proportion of the matrix material in the emitting layer in this caseis between 50.0% and 99.9% by volume, preferably between 80.0% and 99.5%by volume, and more preferably between 92.0% and 99.5% by volume forfluorescent emitting layers and between 85.0% and 97.0% by volume forphosphorescent emitting layers.

Correspondingly, the proportion of the dopant is between 0.1% and 50.0%by volume, preferably between 0.5% and 20.0% by volume, and morepreferably between 0.5% and 8.0% by volume for fluorescent emittinglayers and between 3.0% and 15.0% by volume for phosphorescent emittinglayers.

An emitting layer of an organic electroluminescent device may alsocomprise systems comprising a plurality of matrix materials (mixedmatrix systems) and/or a plurality of dopants. In this case too, thedopants are generally those materials having the smaller proportion inthe system and the matrix materials are those materials having thegreater proportion in the system. In individual cases, however, theproportion of a single matrix material in the system may be less thanthe proportion of a single dopant.

In a further preferred embodiment of the invention, the compoundcomprising structures of formula (I) or the preferred embodimentsrecited above and below are used as a component of mixed matrix systems.The mixed matrix systems preferably comprise two or three differentmatrix materials, more preferably two different matrix materials.Preferably, in this case, one of the two materials is a material havinghole-transporting properties and the other material is a material havingelectron-transporting properties. The desired electron-transporting andhole-transporting properties of the mixed matrix components may,however, also be combined mainly or entirely in a single mixed matrixcomponent, in which case the further mixed matrix component(s) fulfil(s)other functions. The two different matrix materials may be present in aratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferably 1:10 to1:1 and most preferably 1:4 to 1:1. Preference is given to using mixedmatrix systems in phosphorescent organic electroluminescent devices. Onesource of more detailed information about mixed matrix systems is theapplication WO 2010/108579.

The present invention further provides an electronic device, preferablyan organic electroluminescent device or an organic electrochemical cell,comprising one or more compounds of the invention and/or at least oneoligomer, polymer or dendrimer of the invention in one or more emittinglayers, as matrix material.

The present invention additionally provides an electronic device,preferably an organic electroluminescent device or an organicelectrochemical cell, comprising one or more compounds of the inventionand/or at least one oligomer, polymer or dendrimer of the invention inone or more emitting layers, as emitter material.

Preferred cathodes are metals having a low work function, metal alloysor multilayer structures composed of various metals, for examplealkaline earth metals, alkali metals, main group metals or lanthanoids(e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable arealloys composed of an alkali metal or alkaline earth metal and silver,for example an alloy composed of magnesium and silver. In the case ofmultilayer structures, in addition to the metals mentioned, it is alsopossible to use further metals having a relatively high work function,for example Ag, in which case combinations of the metals such as Mg/Ag,Ca/Ag or Ba/Ag, for example, are generally used. It may also bepreferable to introduce a thin interlayer of a material having a highdielectric constant between a metallic cathode and the organicsemiconductor. Examples of useful materials for this purpose are alkalimetal or alkaline earth metal fluorides, but also the correspondingoxides or carbonates (e.g. LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃,etc.). Likewise useful for this purpose are organic alkali metalcomplexes, e.g. Liq (lithium quinolinate). The layer thickness of thislayer is preferably between 0.5 and 5 nm.

Preferred anodes are materials having a high work function. Preferably,the anode has a work function of greater than 4.5 eV versus vacuum.Firstly, metals having a high redox potential are suitable for thispurpose, for example Ag, Pt or Au. Secondly, metal/metal oxideelectrodes (e.g. Al/Ni/NiO_(x), Al/PtO_(x)) may also be preferred. Forsome applications, at least one of the electrodes has to be transparentor partly transparent in order to enable either the irradiation of theorganic material (O-SC) or the emission of light (OLED/PLED, O-laser).Preferred anode materials here are conductive mixed metal oxides.Particular preference is given to indium tin oxide (ITO) or indium zincoxide (IZO). Preference is further given to conductive doped organicmaterials, especially conductive doped polymers, for example PEDOT, PANIor derivatives of these polymers. It is further preferable when ap-doped hole transport material is applied to the anode as holeinjection layer, in which case suitable p-dopants are metal oxides, forexample MoO₃ or WO₃, or (per)fluorinated electron-deficient aromaticsystems. Further suitable p-dopants are HAT-CN(hexacyanohexaazatriphenylene) or the compound NPD9 from Novaled. Such alayer simplifies hole injection into materials having a low HOMO, i.e. alarge HOMO in terms of magnitude.

In the further layers, it is generally possible to use any materials asused according to the prior art for the layers, and the person skilledin the art is able, without exercising inventive skill, to combine anyof these materials with the materials of the invention in an electronicdevice.

The device is correspondingly (according to the application) structured,contact-connected and finally hermetically sealed, since the lifetime ofsuch devices is severely shortened in the presence of water and/or air.

Additionally preferred is an electronic device, especially an organicelectroluminescent device, which is characterized in that one or morelayers are coated by a sublimation process. In this case, the materialsare applied by vapour deposition in vacuum sublimation systems at aninitial pressure of typically less than 10-5 mbar, preferably less than10⁻⁶ mbar. It is also possible that the initial pressure is even loweror even higher, for example less than 10-7 mbar.

Preference is likewise given to an electronic device, especially anorganic electroluminescent device, which is characterized in that one ormore layers are coated by the OVPD (organic vapour phase deposition)method or with the aid of a carrier gas sublimation. In this case, thematerials are applied at a pressure between 10-5 mbar and 1 bar. Aspecial case of this method is the OVJP (organic vapour jet printing)method, in which the materials are applied directly by a nozzle and thusstructured (for example M. S. Arnold et al., Appl. Phys. Lett. 2008, 92,053301).

Preference is additionally given to an electronic device, especially anorganic electroluminescent device, which is characterized in that one ormore layers are produced from solution, for example by spin-coating, orby any printing method, for example screen printing, flexographicprinting, offset printing or nozzle printing, but more preferably LITI(light-induced thermal imaging, thermal transfer printing) or inkjetprinting. For this purpose, soluble compounds are needed, which areobtained, for example, through suitable substitution.

The electronic device, especially the organic electroluminescent device,can also be produced as a hybrid system by applying one or more layersfrom solution and applying one or more other layers by vapourdeposition. For example, it is possible to apply an emitting layercomprising a compound of the invention comprising structures of formula(I) and a matrix material from solution, and to apply a hole blockerlayer and/or an electron transport layer thereto by vapour depositionunder reduced pressure.

These methods are known in general terms to those skilled in the art andcan be applied without difficulty to electronic devices, especiallyorganic electroluminescent devices comprising compounds of the inventioncomprising structures of formula (I) or the above-detailed preferredembodiments.

The electronic devices of the invention, especially organicelectroluminescent devices, are notable for one or more of the followingsurprising advantages over the prior art:

-   -   1. Electronic devices, especially organic electroluminescent        devices and very particularly organic light-emitting diodes or        organic light-emitting electrochemical cells, comprising        compounds, oligomers, polymers or dendrimers having structures        of formula (I) or the preferred embodiments recited above and        hereinafter, especially as electron-conducting materials, have a        very good lifetime.    -   2. Electronic devices, especially organic electroluminescent        devices and very particularly organic light-emitting diodes or        organic light-emitting electrochemical cells, comprising        compounds, oligomers, polymers or dendrimers having structures        of formula (I) or the preferred embodiments recited above and        hereinafter, as electron-conducting materials, electron        injection materials and/or host materials, have excellent        efficiency. More particularly, efficiency is much higher        compared to analogous compounds containing no structural unit of        formula (I). In this context, compounds, oligomers, polymers or        dendrimers of the invention having structures of formula (I) or        the preferred embodiments recited above and hereinafter bring        about a low operating voltage when used in electronic devices.        In this context, these compounds especially bring about low        roll-off, i.e. a small drop in power efficiency of the device at        high luminances.    -   3. The compounds, oligomers, polymers or dendrimers of the        invention having structures of formula (I) or the preferred        embodiments recited above and hereinafter exhibit very high        stability (for example redox stability, thermal stability and        photochemical stability) and lead to compounds having a very        long lifetime.    -   4. With compounds, oligomers, polymers or dendrimers having        structures of formula (I) or the preferred embodiments recited        above and hereinafter, it is possible to avoid the formation of        optical loss channels in electronic devices, especially organic        electroluminescent devices and very particularly organic        light-emitting diodes or organic light-emitting electrochemical        cells. As a result, these devices feature a high PL efficiency        and hence high EL efficiency of emitters, and excellent energy        transmission of the matrices to dopants.    -   5. The use of compounds, oligomers, polymers or dendrimers        having structures of formula (I) or the preferred embodiments        recited above and hereinafter in layers of electronic devices,        especially organic electroluminescent devices and very        particularly organic light-emitting diodes or organic        light-emitting electrochemical cells, leads to high mobility of        the electron conductor structures.    -   6. Compounds, oligomers, polymers or dendrimers having        structures of formula (I) or the preferred embodiments recited        above and below feature excellent thermal stability, and        compounds having a molar mass of less than about 1200 g/mol have        good sublimability.    -   7. Compounds, oligomers, polymers or dendrimers having        structures of formula (I) or the preferred embodiments recited        above and hereinafter have excellent glass film formation.    -   8. Compounds, oligomers, polymers or dendrimers having        structures of formula (I) or the preferred embodiments recited        above and hereinafter form very good films from solutions.    -   9. The compounds, oligomers, polymers or dendrimers comprising        structures of formula (I) or the preferred embodiments recited        above and hereinafter have a surprisingly high triplet level T₁,        this being particularly true of compounds which are used as        electron-conducting materials.

These abovementioned advantages are not accompanied by a deteriorationin the further electronic properties.

The compounds and mixtures of the invention are suitable for use in anelectronic device. An electronic device is understood to mean a devicecontaining at least one layer containing at least one organic compound.The component may also comprise inorganic materials or else layersformed entirely from inorganic materials.

The present invention therefore further provides for the use of thecompounds or mixtures of the invention in an electronic device,especially in an organic electroluminescent device.

The present invention still further provides for the use of a compoundof the invention and/or of an oligomer, polymer or dendrimer of theinvention in an electronic device as TADF material, host material, holeconductor material, electron injection material and/or electrontransport material, preferably as TADF material, host material, holeconductor material and/or electron transport material.

The present invention still further provides an electronic devicecomprising at least one of the above-detailed compounds or mixtures ofthe invention.

In this case, the preferences detailed above for the compound also applyto the electronic devices. Particular preference is given to anelectronic device selected from the group consisting of organicelectroluminescent devices (OLEDs, PLEDs), organic integrated circuits(O-ICs), organic field-effect transistors (O-FETs), organic thin-filmtransistors (O-TFTs), organic light-emitting transistors (O-LETs),organic solar cells (O-SCs), organic optical detectors, organicphotoreceptors, organic field-quench devices (O-FQDs), organicelectrical sensors, light-emitting electrochemical cells (LECs),preferably organic light-emitting electrochemical cells (OLECs), organiclaser diodes (O-lasers) and organic plasmon emitting devices (D. M.Koller et al., Nature Photonics 2008, 1-4), preferably organicelectroluminescent devices (OLEDs, PLEDs) or organic light-emittingelectrochemical cells (OLECs), especially phosphorescent or fluorescentOLEDs or fluorescent OLECs.

In a further embodiment of the invention, the organic electroluminescentdevice of the invention does not contain any separate hole injectionlayer and/or hole transport layer and/or hole blocker layer and/orelectron transport layer, meaning that the emitting layer directlyadjoins the hole injection layer or the anode, and/or the emitting layerdirectly adjoins the electron transport layer or the electron injectionlayer or the cathode, as described, for example, in WO 2005/053051. Itis additionally possible to use a metal complex identical or similar tothe metal complex in the emitting layer as hole transport or holeinjection material directly adjoining the emitting layer, as described,for example, in WO 2009/030981.

In addition, it is possible to use the compounds of the invention in anelectron transport layer.

In the further layers of the organic electroluminescent device of theinvention, it is possible to use any materials as typically usedaccording to the prior art. The person skilled in the art is thereforeable, without exercising inventive skill, to use any materials known fororganic electroluminescent devices in combination with the inventivecompounds of formula (I) or according to the preferred embodiments.

The compounds of the invention generally have very good properties onuse in organic electroluminescent devices. Especially in the case of useof the compounds of the invention in organic electroluminescent devices,the lifetime is significantly better compared to similar compoundsaccording to the prior art. At the same time, the further properties ofthe organic electroluminescent device, especially the efficiency andvoltage, are likewise better or at least comparable.

It should be pointed out that variations of the embodiments described inthe present invention are covered by the scope of this invention. Anyfeature disclosed in the present invention may, unless this isexplicitly ruled out, be exchanged for alternative features which servethe same purpose or an equivalent or similar purpose. Thus, any featuredisclosed in the present invention, unless stated otherwise, should beconsidered as an example of a generic series or as an equivalent orsimilar feature.

All features of the present invention may be combined with one anotherin any manner, unless particular features and/or steps are mutuallyexclusive. This is especially true of preferred features of the presentinvention. Equally, features of non-essential combinations may be usedseparately (and not in combination).

It should also be pointed out that many of the features, and especiallythose of the preferred embodiments of the present invention, shouldthemselves be regarded as inventive and not merely as some of theembodiments of the present invention. For these features, independentprotection may be sought in addition to or as an alternative to anycurrently claimed invention.

The technical teaching disclosed with the present invention may beabstracted and combined with other examples.

The invention is illustrated in detail by the examples which follow,without r: any intention of restricting it thereby.

The person skilled in the art will be able to use the details given,without exercising inventive skill, to produce further electronicdevices of the invention and hence to execute the invention over theentire scope claimed.

EXAMPLES

The syntheses which follow, unless stated otherwise, are conducted undera protective gas atmosphere in dried solvents. The metal complexes areadditionally handled with exclusion of light or under yellow light. Thesolvents and reagents can be purchased, for example, from Sigma-ALDRICHor ABCR. The respective figures in square brackets or the numbers quotedfor individual compounds relate to the CAS numbers of the compoundsknown from the literature.

Synthesis of the Synthons Example S1

Procedure analogous to A. Sagadevan, et al., Green Chemistry, 17(2),1113-1119; 2015. To a well-stirred mixture of 16.7 g (100 mmol) ofcarbazole [86-74-8], 34.6 g (250 mmol) of potassium carbonate, 2.5 g (10mmol) of copper(II) sulfate pentahydrate [7758-99-8], 3.6 g (20 mmol) ofphenanthroline, 300 ml of toluene and 50 g of glass beads are added 33.8g (130 mmol) of 1-bromo-4-(2-bromethynyl)benzene [934-94-1], and thenthe mixture is stirred at 80° C. for 16 h. After cooling, the mixture isfiltered through a Celite bed, the latter is washed through and thefiltrate is concentrated to dryness. The residue is purified by flashchromatography (CombiFlash Torrent from Axel Semrau). Yield: 23.2 g (67mmol), 67%; purity: 95% by ¹H NMR.

Example S100

A mixture of 34.6 g (100 mmol) of S1, 38.5 g (100 mmol) of2,3,4,5-tetraphenyl-2,4-cyclopentadien-1-one [479-33-4] and 130 ml ofdiphenyl ether is heated to 265° C. for 24 h. After cooling and removalof the diphenyl ether under reduced pressure, the residue is extractedby boiling with 300 ml of ethanol, and the solids are filtered off withsuction, washed three times with 100 ml each time of EtOH and driedunder reduced pressure. The residue is purified by flash chromatography(CombiFlash Torrent from Axel Semrau). Yield: 51.4 g (73 mmol), 73%;purity: 98% by ¹H NMR.

In an analogous manner, it is possible to prepare the followingcompounds using S1, i.e. 1-bromo-4-[2-(4-chlorophenyl)ethynyl]benzene[832744-28-2], as dienophile:

Ex. Diene Product Yield S101

54% S102

56% S103

52% S104

63% S105

43% S106

55% S107

53%

S108

67% S109

60% S110

63% S111

68% S112

73% S113

69% S114

57% S115

53% S116

62% S117

43% S118

66% S119

60%

S120

67% S121

61%

S122

63%

S123

48%

Example S200: Buchwald Coupling

A mixture of 54.6 g (100 mmol) of S104, 16.7 g (100 mmol) of carbazole[86-74-8], 41.5 g (300 mmol) of potassium carbonate, 50 g of glassbeads, 700 ml of toluene, 405 mg (2 mmol) of tri-tert-butylphosphine and225 mg (1 mmol) of palladium acetate is heated under reflux with goodstirring for 24 h. After cooling, the salts are filtered off withsuction through a Celite bed in the form of a toluene slurry, the bed iswashed through three times with 100 ml each time of warm toluene, andthe filtrate is washed once with 500 ml of water and once with 300 ml ofsodium chloride solution and dried over magnesium sulfate. The solidsobtained after the desiccant has been filtered off and the solvent hasbeen removed are chromatographed (silica gel, dichloromethane) and thenrecrystallized from dimethylacetamide (DMAC). Yield: 46.1 g (73 mmol),73%; purity: 97% by ¹H NMR.

In an analogous manner, it is possible to prepare the followingcompounds, using 120 mmol of sodium tert-butoxide rather than potassiumcarbonate for couplings with secondary amines.

Ex. Reactants Product Yield S201 S104 122-39-4

58% S202 S104 1421789-16-3

70% S203 S104 205-25-4

68% S204 S105 56525-79-2

67% S205 S106 1257220-47-5

72% S206 S107 1466521-76-5

49%

S207 S108 1257247-94-1

59% S208 S108 1431284-23-9

55% S209 S108 1316311-27-9

60% S210 S109 1024598-06-8

38% S211 S110 1199350-22-5

70% S212 S111 1382955-10-3

64% S213 S111 1060735-14-9

60% S214 S112 1609088-05-2

59% S215 S113 244-76-8

68% S216 S114 88590-00-5

45% S217 S115 244-63-3

48% S218 S116 1365647-82-0

58% S219 S117 135-67-1

62% S220 S118 1799501-71-5

60% S221 S119 955959-89-4

49%

S222 S120 1346669-46-2

55% S223 S121 1364890-88-9

47%

S224 S122 1807860-07-6

51%

S225 S123 1372775-52-4

45%

Example S300: Borylation

To a mixture of 70.3 g (100 mmol) of S100, 26.7 g (105 mmol) of4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane)[73183-34-3], 29.5 g (300 mmol) of anhydrous potassium acetate, 50 g ofglass beads (diameter 3 mm) and 700 ml of dioxane are added 543 mg (1.3mmol) of S-Phos [657408-07-6] and 225 mg (1 mmol) of palladium(II)acetate, and the mixture is heated to 90° C. with good stirring for 16h. After cooling, the mixture is filtered through a Celite bed in theform of a dioxane slurry, the bed is washed through with 300 ml ofdioxane, the filtrate is concentrated to dryness, the residue is takenup in 500 ml of toluene, and the solution is washed three times with 100ml each time of water and once with 200 ml of saturated sodium chloridesolution and then dried over magnesium sulfate.

The foam obtained after the desiccant has been filtered off and thesolvent has been removed is recrystallized from ethyl acetate/methanol.Yield: 65.2 g (87 mmol), 87%; purity: 95% by ¹H NMR.

In an analogous manner, it is possible to prepare the followingcompounds:

Ex. Reactant Product Yield S301 S101

89% S302 S102

90% S303 S103

85% S304 S201

86% S305 S202

83% S306 S203

90% S307 S204

86% S308 S205

87% S309 S206

73%

S310 S207

79% S311 S208

80% S312 S209

85% S313 S210

85% S314 S211

87% S315 S212

86% S316 S213

88% S317 S214

79% S318 S215

81% S319 S216

90% S320 S217

80% S321 S218

88% S322 S219

74% S323 S220

82% S324 S221

76%

S325 S222

69% S326 S223

S327 S224

67%

S328 S225

71%

Example P1: Suzuki Coupling

To a well-stirred mixture of 75.0 g (100 mmol) of S300, 28.1 g (105mmol) of 1-chloro-3,5-diphenyltriazine [3842-55-5], 63.7 g (300 mmol) oftripotassium phosphate, 500 ml of toluene, 300 ml of dioxane, 500 ml ofwater are added 1.2 g (3 mmol) of S-Phos [657408-07-6] and 498 mg (2mmol) of palladium(II) acetate, and then the mixture is heated underreflux for 16 h. After cooling, the organic phase is removed and washedtwice with 300 ml each time of water and once with 300 ml of saturatedsodium chloride solution, and then dried over magnesium sulfate. Thedesiccant is filtered off through a Celite bed in the form of a tolueneslurry, the bed is washed through with 300 ml of toluene, the filtrateis concentrated to dryness and the residue is crystallized twice fromdimethylacetamide. Further purification is effected by repeated hotextraction with n-butyl acetate, followed by fractional sublimation (pabout 10⁻⁵ mbar, T about 33000). Yield: 47.9 g (56 mmol), 56%; purity:99.9% by ¹H NMR.

In an analogous manner, it is possible to prepare the followingcompounds, with products of molar mass greater than 1200 g/mol typicallybeing freed of residual solvents by heating under high vacuum:

Ex. Reactant Product Yield P2  S101 1215596-23-6

54% P3  S102 1613163-88-4

49% P4  S303 2915-16-4

59% P5  S304 3842-55-5

57% P6  S305 2915-16-4

53% P7  S306 29874-83-7

55% P8  S307 1300115-09-6

51% P9  S308 6484-25-9

49% P10 S309 24547-45-3

38%

P11 S310 23449-08-3

55% P12 S311 864377-31-1

58% P13 S312 1616231-57-2

54% P14 S313 1689576-03-1

50% P15 S314 55635-65-9

57% P16 S315 1931136-94-5

51% P17 S316 3842-55-5

53% P18 S317 3842-55-5

59% P19 S318 1439929-51-7

55% P20 S319 334-04-7

52% P21 S320 371-88-6

56% P22 S321 80587-76-4

49% P23 S322 37084-03-4

44% P24 S323 334-04-7

47% P25 S324 3842-55-5

30%

P26 S325 3842-55-5

P27 S326 15679-03-5

32%

P28 S327 3842-55-5

27%

P29 S328 3842-55-5

29%

Example: Production of the OLEDs

1) Vacuum-Processed Devices:

OLEDs of the invention and OLEDs according to the prior art are producedby a general method according to WO 2004/058911, which is adapted to thecircumstances described here (variation in layer thickness, materialsused).

In the examples which follow, the results for various OLEDs arepresented. Glass plaques with structured ITO (50 nm, indium tin oxide)form the substrates to which the OLEDs are applied. The OLEDs basicallyhave the following layer structure: substrate/hole transport layer 1(HTL1) consisting of HTM doped with 5% NDP-9 (commercially availablefrom Novaled), 20 nm/hole transport layer 2 (HTL2)/optional electronblocker layer (EBL)/emission layer (EML)/optional hole blocker layer(HBL)/electron transport layer (ETL)/optional electron injection layer(EIL) and finally a cathode. The cathode is formed by an aluminium layerof thickness 100 nm.

First of all, vacuum-processed OLEDs are described. For this purpose,all the materials are applied by thermal vapour deposition in a vacuumchamber. In this case, the emission layer always consists of at leastone matrix material (host material) and an emitting dopant (emitter)which is added to the matrix material(s) in a particular proportion byvolume by co-evaporation. Details given in such a form as M3:M2:Ir(L2)(55%:35%:10%) mean here that the material M3 is present in the layer ina proportion by volume of 55%, M2 in a proportion of 35% and Ir(L2) in aproportion of 10%. Analogously, the electron transport layer may alsoconsist of a mixture of two materials. The exact structure of the OLEDscan be found in Table 1. The materials used for production of the OLEDsare shown in Table 4.

The OLEDs are characterized in a standard manner. For this purpose, theelectroluminescence spectra, the power efficiency (measured in cd/A) andthe voltage (measured at 1000 cd/m² in V) are determined fromcurrent-voltage-brightness characteristics (IUL characteristics). Forselected experiments, the lifetime is determined. The lifetime isdefined as the time after which the luminance has fallen from aparticular starting luminance to a certain proportion. The figure LD50means that the lifetime specified is the time at which the luminance hasdropped to 50% of the starting luminance, i.e. from, for example, 1000cd/m² to 500 cd/m². According to the emission colour, different startingbrightnesses were selected. The values for the lifetime can be convertedto a figure for other starting luminances with the aid of conversionformulae known to those skilled in the art. In this context, thelifetime for a starting luminance of 1000 cd/m² is a standard figure.

Use of Compounds of the Invention as Emitter Materials in PhosphorescentOLEDs

One use of the compounds of the invention is as emitter materials (TADF)in the emission layer in OLEDs.

They are also usable as matrix/host material for phosphorescentemitters. The compounds according to Table 4 are used as a comparisonaccording to the prior art. The results for the OLEDs are collated inTable 2.

TABLE 1 Structure of the OLEDs HTL2 EBL HBL thick- thick- EML thick- ETLEx. ness ness thickness ness thickness Ref.-D1 HTM — M1:IrRef1 HBM1ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D1 HTM — P1:IrRef1HBM1 ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D2 HTM —P4:IrRef1 HBM1 ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D3HTM — P4:IrRef1 HBM1 ETM1:ETM2 40 nm (80%:20%) (50%:50%) 35 nm 30 nm D4HTM — P4:M3:IrRef1 HBM1 ETM1:ETM2 40 nm (60%:30%:10%) 10 nm (50%:50%) 35nm 30 nm D5 HTM — P18:M3 HBM1 ETM1:ETM2 40 nm (60%:40%) 10 nm (50%:50%)40 nm 30 nm D6 HTM — P18:M3:SER1 HBM1 ETM1:ETM2 40 nm (60%:35%:5%) 10 nm(50%:50%) 40 nm 30 nm

TABLE 2 Results for the vacuum-processed OLEDs EQE (%) Voltage (V) CIEx/y LD50 (h) Ex. 1000 cd/m² 1000 cd/m² 1000 cd/m² 1000 cd/m² Ref.-D118.8 3.2 0.34/0.62 190000 D1 18.9 3.0 0.33/0.62 240000 D2 19.2 2.90.34/0.62 230000 D3 19.4 2.9 0.33/0.63 340000 D4 19.0 3.1 0.34/0.62360000 EQE (%) Voltage (V) CIE x/y LD50 (h) Ex. 500 cd/m² 500 cd/m² 500ccd/m² 500 cd/m² D5 12.3 3.4 0.26/0.54 20000 D6 15.7 3.5 0.51/0.47 90000

Solution-Processed Devices:

From Soluble Functional Materials of Low Molecular Weight

The iridium complexes of the invention may also be processed fromsolution and lead therein to OLEDs which are much simpler in terms ofprocess technology compared to the vacuum-processed OLEDs, butnevertheless have good properties. The production of such components isbased on the production of polymeric light-emitting diodes (PLEDs),which has already been described many times in the literature (forexample in WO 2004/037887). The structure is composed ofsubstrate/ITO/hole injection layer (60 nm)/interlayer (20 nm)/emissionlayer (60 nm)/hole blocker layer (10 nm)/electron transport layer (40nm)/cathode. For this purpose, substrates from Technoprint (soda-limeglass) are used, to which the ITO structure (indium tin oxide, atransparent conductive anode) is applied. The substrates are cleaned ina cleanroom with DI water and a detergent (Deconex 15 PF) and thenactivated by a UV/ozone plasma treatment. Thereafter, likewise in acleanroom, a 20 nm hole injection layer is applied by spin-coating. Therequired spin rate depends on the degree of dilution and the specificspin-coater geometry. In order to remove residual water from the layer,the substrates are baked on a hotplate at 200° C. for 30 minutes. Theinterlayer used serves for hole transport, in this case, HL-X from Merckis used. The interlayer may alternatively also be replaced by one ormore layers which merely have to fulfil the condition of not beingleached off again by the subsequent processing step of EML depositionfrom solution. For production of the emission layer, the tripletemitters of the invention are dissolved together with the matrixmaterials in toluene or chlorobenzene. The typical solids content ofsuch solutions is between 16 and 25 g/I when, as here, the layerthickness of 60 nm which is typical of a device is to be achieved bymeans of spin-coating. The solution-processed green type 1 devicescontain an emission layer composed of P:M:IrRef2 (X %:Y %:Z %); the redtype 2 devices contain an emission layer composed of P:M:IrRef2:IrRef3(X %:Y %:Z %:5%); in other words, they contain two different Ircomplexes. The emission layer is spun on in an inert gas atmosphere,argon in the present case, and baked at 160° C. for 10 min.Vapour-deposited above the latter are the hole blocker layer (10 nmETM1) and the electron transport layer (40 nm ETM1 (50%)/ETM2 (50%))(vapour deposition systems from Lesker or the like, typical vapourdeposition pressure 5×10⁻⁶ mbar). Finally, a cathode of aluminium (100nm) (high-purity metal from Aldrich) is applied by vapour deposition. Inorder to protect the device from air and air humidity, the device isfinally encapsulated and then characterized. The OLED examples cited areyet to be optimized; Table 3 summarizes the data obtained.

TABLE 3 Results with materials processed from solution EQE Voltage LD50(%) (V) (h) 1000 1000 CIE 1000 Ex. P:M:IrRef cd/m² cd/m² x/y cd/m² Redtype 2 devices Sol-Ref-Red1 M4:M5:IrRef2 17.4 6.2 0.66/0.34 24000030%:40%:25% Sol-RedD1 P11:M5:IrRef2 18.3 5.8 0.66/0.34 29000070%:0%:25%  Sol-RedD2 P11:M5:IrRef2 18.6 5.9 0.66/0.34 32000050%:20%:25% Sol-RedD3 P28:M5:IrRef2 18.8 6.1 0.66/0.34 37000070%:0%:25%  Green type 1 devices Sol-Ref-Green1 M4:M5:IrRef2 20.1 5.30.33/0.62 200000 20%:60%:20% Sol-GreenD1 P10:M5:IrRef2 20.6 54 0.33/0.62230000 80%:0%20%  Sol-GreenD2 P10:M5:IrRef2 20.9 5.3 0.33/0.62 22000050%:30%:20% Sol-GreenD3 P11:M5:IrRef2 20.8 5.1 0.33/0.62 24000060%:20%:20% Sol-GreenD4 P13:M5:IrRef2 20.5 5.2 0.33/0.62 24000050%:30%:25% Sol-GreenD5 P14:M4:IrRef2 20.2 5.0 0.34/0.61 25000045%:30%:25% Sol-GreenD6 P18:M3:IrRerf2 20.0 52 0.32/0.63 31000050%:35%:15% Sol-GreenD7 P25:M5:IrRef2 19.9 5.1 0.33/0.62 26000080%:0%:20%  Sol-GreenD8 P28:M5:IrRef2 20.3 5.0 0.32/0.62 24000075%:0%:25% 

TABLE 4 Structural formulae of the materials used

1.-19. (canceled)
 20. A compound comprising at least one structure ofthe formula (I):

where the symbols used are as follows: Q is an acceptor group comprisingan aromatic or heteroaromatic ring system which has 5 to 60 aromaticring atoms and may be substituted by one or more R¹ radicals; HL is adonor group; Ar^(a), Ar^(b) is the same or different and is an aromaticor heteroaromatic ring system which has 5 to 60 aromatic ring atoms andmay be substituted by one or more R¹ radicals; R^(a), R^(b) is the sameor different and is a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R¹ radicals, where one or more nonadjacentCH₂ groups may be replaced by —R¹C═CR¹—, —C—C—, Si(R¹)₂, Ge(R¹)₂,Sn(R¹)₂, C═O, C═S, C═Se, C═NR¹, NR¹, P(═O)(R¹), —C(═O)O—, —C(═O)NR¹—,—O—, —S—, SO or SO₂ and where one or more hydrogen atoms may be replacedby D, F, Cl, Br, I, CN or NO₂, or an aromatic or heteroaromatic ringsystem which has 5 to 60 aromatic ring atoms and may be substituted ineach case by one or more R¹ radicals, or an aryloxy or heteroaryloxygroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R¹ radicals, or an aralkyl or heteroaralkyl group which has5 to 60 aromatic ring atoms and may be substituted by one or more R¹radicals, or a diarylamino group, diheteroarylamino group orarylheteroarylamino group which has 10 to 40 aromatic ring atoms and maybe substituted by one or more R¹ radicals; or a combination of thesesystems; at the same time, the R^(a) and R^(b) together form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem; R¹ is the same or different at each instance and is H, D, F, Cl,Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂,Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R²radicals, where one or more nonadjacent CH₂ groups may be replaced by—R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R² radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R² radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R² radicals;or a combination of these systems; at the same time, two or more R¹radicals together may form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R² is the sameor different at each instance and is H, D, F, Cl, Br, I, B(OR³)₂, CHO,C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂,P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R³ radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R³C═CR³—, —C—C—,Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³,P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R³ radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R³ radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R³ radicals,or a combination of these systems; at the same time, two or more R²substituents together may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; and R³ is thesame or different at each instance and is H, D, F or an aliphatic,aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbonatoms, in which hydrogen atoms may also be replaced by F; at the sametime, two or more R³ substituents together may also form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem.
 21. The compound according to claim 20, wherein the Ar^(a)and/or Ar^(b) group in formula (I) is different from a donor group asper symbol HL.
 22. The compound according to claim 20, wherein the donorgroup HL comprises a group selected from the formulae (H-1) to (H-3)

where the dotted bond marks the attachment position and Ar², Ar³, Ar⁴are each independently an aryl group having 6 to 40 carbon atoms or aheteroaryl group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R radicals; p is 0, 1, 2, 3, 4, 5 or 6; Z isCR¹ ₂, SiR¹ ₂, C═O, N-Ar¹, BR¹, PR¹, POR¹, SO, SO₂, Se, O or S; R¹ isthe same or different at each instance and is H, D, F, Cl, Br, I,B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂, Si(R²)₃,N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R²radicals, where one or more nonadjacent CH₂ groups may be replaced by—R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R² radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R² radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R² radicals;or a combination of these systems; at the same time, two or more R¹radicals together may form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R² is the sameor different at each instance and is H, D, F, Cl, Br, I, B(OR³)₂, CHO,C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂,P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R³ radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R³C═CR³—, —C—C—,Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³,P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R³ radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R³ radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R³ radicals,or a combination of these systems; at the same time, two or more R²substituents together may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R³ is the sameor different at each instance and is H, D, F or an aliphatic, aromaticand/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms,in which hydrogen atoms may also be replaced by F; at the same time, twoor more R³ substituents together may also form a mono- or polycyclic,aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; andAr¹ represents an aromatic or heteroaromatic ring system which has 5 to60 aromatic ring atoms and may be substituted in each case by one ormore R¹ radicals, an aryloxy group which has 5 to 60 aromatic ring atomsand may be substituted in each case by one or more R¹ radicals, or anaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted in each case by one or more R¹ radicals, where it isoptionally possible for two or more, R¹ substituents to form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem which may be substituted by one or more R³ radicals.
 23. Thecompound according to claim 20, wherein the donor group HL comprises agroup selected from the formulae (H-4) to (H-26)

wherein Y¹ represents O, S, C(R¹)₂ or NAr¹; the dotted bond marks theattachment position; e is 0, 1 or 2; j is 0, 1, 2 or 3; h is 0, 1, 2, 3or 4; p is 0, 1, 2, 3, 4, 5 or 6; Ar¹ represents an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R¹ radicals, an aryloxy groupwhich has 5 to 60 aromatic ring atoms and may be substituted in eachcase by one or more R¹ radicals, or an aralkyl group which has 5 to 60aromatic ring atoms and may be substituted in each case by one or moreR¹ radicals, where it is optionally possible for two or more, R¹substituents to form a mono- or polycyclic, aliphatic, heteroaliphatic,aromatic or heteroaromatic ring system which may be substituted by oneor more R³ radicals; Ar² is an aryl group having 6 to 40 carbon atoms ora heteroaryl group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R¹ radicals; R¹ is the same or different ateach instance and is H, D, F, Cl, Br, I, B(OR²)₂, CHO, C(═O)R²,CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂,OSO₂R², OR², S(═O)R², S(═O)₂R², a straight-chain alkyl, alkoxy orthioalkoxy group having 1 to 40 carbon atoms or a branched or cyclicalkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each ofwhich may be substituted by one or more R² radicals, where one or morenonadjacent CH₂ groups may be replaced by —R²C═CR²—, —C—C—, Si(R²)₂,Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR², P(═O)(R²), —C(═O)O—,—C(═O)NR²—, —O—, —S—, SO or SO₂ and where one or more hydrogen atoms maybe replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R² radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R² radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R² radicals; or a combination of thesesystems; at the same time, two or more R¹ radicals together may form amono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; R² is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN,C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³,S(═O)R³, S(═O)₂R³, a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R³ radicals, where one or more nonadjacentCH₂ groups may be replaced by —R³C═CR³—, —C—C—, Si(R³)₂, Si(R³)₂,Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³, P(═O)(R³), —C(═O)O—,—C(═O)NR³—, —O—, —S—, SO or SO₂ and where one or more hydrogen atoms maybe replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R³ radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R³ radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R³ radicals, or a combination of thesesystems; at the same time, two or more R² substituents together may alsoform a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; and R³ is the same or different at eachinstance and is H, D, F or an aliphatic, aromatic and/or heteroaromatichydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atomsmay also be replaced by F; at the same time, two or more R³ substituentstogether may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system.
 24. Thecompound according to claim 22, wherein the Ar² group is a connectingstructure of the formula (LAr-1)

where X is the same or different at each instance and is N or CR¹, or Cif a group binds to X; the dotted bond marks the attachment position; sis 0, 1, 2, 3, 4, 5 or 6; R¹ is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN,C(═O)OR², C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR²,S(═O)R², S(═O)₂R², a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R² radicals, where one or more nonadjacentCH₂ groups may be replaced by —R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂,Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR², P(═O)(R²), —C(═O)O—, —C(═O)NR²—,—O—, —S—, SO or SO₂ and where one or more hydrogen atoms may be replacedby D, F, Cl, Br, I, CN or NO₂, or an aromatic or heteroaromatic ringsystem which has 5 to 60 aromatic ring atoms and may be substituted ineach case by one or more R² radicals, or an aryloxy or heteroaryloxygroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R² radicals, or an aralkyl or heteroaralkyl group which has5 to 60 aromatic ring atoms and may be substituted by one or more R²radicals, or a diarylamino group, diheteroarylamino group orarylheteroarylamino group which has 10 to 40 aromatic ring atoms and maybe substituted by one or more R² radicals; or a combination of thesesystems; at the same time, two or more R¹ radicals together may form amono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; R² is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN,C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³,S(═O)R³, S(═O)₂R³, a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R³ radicals, where one or more nonadjacentCH₂ groups may be replaced by —R³C═CR³—, —C—C—, Si(R³)₂, Si(R³)₂,Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³, P(═O)(R³), —C(═O)O—,—C(═O)NR³—, —O—, —S—, SO or SO₂ and where one or more hydrogen atoms maybe replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R³ radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R³ radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R³ radicals, or a combination of thesesystems; at the same time, two or more R² substituents together may alsoform a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; and R³ is the same or different at eachinstance and is H, D, F or an aliphatic, aromatic and/or heteroaromatichydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atomsmay also be replaced by F; at the same time, two or more R³ substituentstogether may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system.
 25. Thecompound according to claim 22, wherein the acceptor group is a groupthat can be represented by the formula (QL)Q¹-L¹-  Formula (QL) in which L¹ represents a bond or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted by one or more R¹ radicals; Q¹ is an electron-withdrawinggroup; R¹ is the same or different at each instance and is H, D, F, Cl,Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂,Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R²radicals, where one or more nonadjacent CH₂ groups may be replaced by—R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R² radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R² radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R² radicals;or a combination of these systems; at the same time, two or more R¹radicals together may form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R² is the sameor different at each instance and is H, D, F, Cl, Br, I, B(OR³)₂, CHO,C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂,P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R³ radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R³C═CR³—, —C—C—,Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³,P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R³ radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R³ radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R³ radicals,or a combination of these systems; at the same time, two or more R²substituents together may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; and R³ is thesame or different at each instance and is H, D, F or an aliphatic,aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbonatoms, in which hydrogen atoms may also be replaced by F; at the sametime, two or more R³ substituents together may also form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem.
 26. The compound according to claim 22, wherein Ar² group is aconnecting structure of the formula (LAr-2)

where X is the same or different at each instance and is N or CR¹, or Cif a group binds to X; the dotted bond marks the attachment position andt is 0, 1, 2, 3, 4, 5 or 6; R¹ is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN,C(═O)OR², C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR²,S(═O)R², S(═O)₂R², a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R² radicals, where one or more nonadjacentCH₂ groups may be replaced by —R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂,Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR², P(═O)(R²), —C(═O)O—, —C(═O)NR²—,—O—, —S—, SO or SO₂ and where one or more hydrogen atoms may be replacedby D, F, Cl, Br, I, CN or NO₂, or an aromatic or heteroaromatic ringsystem which has 5 to 60 aromatic ring atoms and may be substituted ineach case by one or more R² radicals, or an aryloxy or heteroaryloxygroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R² radicals, or an aralkyl or heteroaralkyl group which has5 to 60 aromatic ring atoms and may be substituted by one or more R²radicals, or a diarylamino group, diheteroarylamino group orarylheteroarylamino group which has 10 to 40 aromatic ring atoms and maybe substituted by one or more R² radicals; or a combination of thesesystems; at the same time, two or more R¹ radicals together may form amono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; R² is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN,C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³,S(═O)R³, S(═O)₂R³, a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R³ radicals, where one or more nonadjacentCH₂ groups may be replaced by —R³C═CR³—, —C—C—, Si(R³)₂, Si(R³)₂,Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³, P(═O)(R³), —C(═O)O—,—C(═O)NR³—, —O—, —S—, SO or SO₂ and where one or more hydrogen atoms maybe replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R³ radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R³ radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R³ radicals, or a combination of thesesystems; at the same time, two or more R² substituents together may alsoform a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; and R³ is the same or different at eachinstance and is H, D, F or an aliphatic, aromatic and/or heteroaromatichydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atomsmay also be replaced by F; at the same time, two or more R³ substituentstogether may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system.
 27. Thecompound according to claim 25, wherein the Q¹ group is selected fromstructures of the formulae (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6),(Q-7), (Q-8), (Q-9) and/or (Q-10)

where the dotted bond marks the attachment position; Q′ is the same ordifferent at each instance and represents CR¹ or N; Q″ represents NR¹, Oor S; where at least one Q′ is N and/or at least one Q″ is NR¹; R¹ isthe same or different at each instance and is H, D, F, Cl, Br, I,B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂, Si(R²)₃,N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R²radicals, where one or more nonadjacent CH₂ groups may be replaced by—R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R² radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R² radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R² radicals;or a combination of these systems; at the same time, two or more R¹radicals together may form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R² is the sameor different at each instance and is H, D, F, Cl, Br, I, B(OR³)₂, CHO,C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂,P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R³ radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R³C═CR³—, —C—C—,Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³,P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R³ radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R³ radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R³ radicals,or a combination of these systems; at the same time, two or more R²substituents together may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; and R³ is thesame or different at each instance and is H, D, F or an aliphatic,aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbonatoms, in which hydrogen atoms may also be replaced by F; at the sametime, two or more R³ substituents together may also form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem.
 28. The compound according to claim 25, wherein the Q¹ group isselected from structures of the formulae (Q-11), (Q-12), (Q-13), (Q-14)and/or (Q-15)

wherein R¹ is the same or different at each instance and is H, D, F, Cl,Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂,Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R²radicals, where one or more nonadjacent CH₂ groups may be replaced by—R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR²,P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R² radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R² radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R² radicals;or a combination of these systems; at the same time, two or more R¹radicals together may form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R² is the sameor different at each instance and is H, D, F, Cl, Br, I, B(OR³)₂, CHO,C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂,P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R³ radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R³C═CR³—, —C—C—,Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³,P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ and where one ormore hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or anaromatic or heteroaromatic ring system which has 5 to 60 aromatic ringatoms and may be substituted in each case by one or more R³ radicals, oran aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atomsand may be substituted by one or more R³ radicals, or an aralkyl orheteroaralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or a diarylamino group,diheteroarylamino group or arylheteroarylamino group which has 10 to 40aromatic ring atoms and may be substituted by one or more R³ radicals,or a combination of these systems; at the same time, two or more R²substituents together may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system; R³ is the sameor different at each instance and is H, D, F or an aliphatic, aromaticand/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms,in which hydrogen atoms may also be replaced by F; at the same time, twoor more R³ substituents together may also form a mono- or polycyclic,aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; X isN or CR¹ and the dotted bond marks the attachment position.
 29. Thecompound according to claim 25, wherein the Q¹ group is selected fromstructures of the formulae (Q-26), (Q-27), (Q-28), (Q-29) and/or (Q-30)

wherein X is N or CR¹; R¹ is the same or different at each instance andis H, D, F, Cl, Br, I, B(OR²)₂, CHO, C(═O)R², CR²═C(R²)₂, CN, C(═O)OR²,C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂, P(═O)(R²)₂, OSO₂R², OR², S(═O)R²,S(═O)₂R², a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxygroup having 3 to 40 carbon atoms, each of which may be substituted byone or more R² radicals, where one or more nonadjacent CH₂ groups may bereplaced by —R²C═CR²—, —C—C—, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se,C═NR², NR², P(═O)(R²), —C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ andwhere one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CNor NO₂, or an aromatic or heteroaromatic ring system which has 5 to 60aromatic ring atoms and may be substituted in each case by one or moreR² radicals, or an aryloxy or heteroaryloxy group which has 5 to 60aromatic ring atoms and may be substituted by one or more R² radicals,or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ringatoms and may be substituted by one or more R² radicals, or adiarylamino group, diheteroarylamino group or arylheteroarylamino groupwhich has 10 to 40 aromatic ring atoms and may be substituted by one ormore R² radicals; or a combination of these systems; at the same time,two or more R¹ radicals together may form a mono- or polycyclic,aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R²is the same or different at each instance and is H, D, F, Cl, Br, I,B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN, C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃,N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³, S(═O)R³, S(═O)₂R³, astraight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbonatoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3to 40 carbon atoms, each of which may be substituted by one or more R³radicals, where one or more nonadjacent CH₂ groups may be replaced by—R³C═CR³—, —C—C—, Si(R³)₂, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se,C═NR³, NR³, P(═O)(R³), —C(═O)O—, —C(═O)NR³—, —O—, —S—, SO or SO₂ andwhere one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CNor NO₂, or an aromatic or heteroaromatic ring system which has 5 to 60aromatic ring atoms and may be substituted in each case by one or moreR³ radicals, or an aryloxy or heteroaryloxy group which has 5 to 60aromatic ring atoms and may be substituted by one or more R³ radicals,or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ringatoms and may be substituted by one or more R³ radicals, or adiarylamino group, diheteroarylamino group or arylheteroarylamino groupwhich has 10 to 40 aromatic ring atoms and may be substituted by one ormore R³ radicals, or a combination of these systems; at the same time,two or more R² substituents together may also form a mono- orpolycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ringsystem; R³ is the same or different at each instance and is H, D, F oran aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F;at the same time, two or more R³ substituents together may also form amono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; the dotted bond marks the attachmentposition, and Ar¹ represents an aromatic or heteroaromatic ring systemwhich has 5 to 60 aromatic ring atoms and may be substituted in eachcase by one or more R¹ radicals, an aryloxy group which has 5 to 60aromatic ring atoms and may be substituted by one or more R¹ radicals,or an aralkyl group which has 5 to 60 aromatic ring atoms and may besubstituted in each case by one or more R¹ radicals, where it isoptionally possible for two or more, preferably adjacent R¹ substituentsto form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system which may be substituted by one or more R²radicals.
 30. The compound according to claim 25, wherein theelectron-withdrawing Q¹ group is an aromatic or heteroaromatic ringsystem which has 5 to 60 aromatic ring atoms and has one or moreelectron-withdrawing substituents.
 31. The compound according to claim30, wherein the electron-withdrawing substituent is selected from F,fluorinated alkyl groups, CF₃, C_(n)F_(2n+1), C(═O)OR¹, C(═O)N(R′)₂,NO₂, CHO, C(═O)R¹, S(═O)R¹, S(═O)₂R¹ and/or CN; R¹ is the same ordifferent at each instance and is H, D, F, Cl, Br, I, B(OR²)₂, CHO,C(═O)R², CR²═C(R²)₂, CN, C(═O)OR², C(═O)N(R²)₂, Si(R²)₃, N(R²)₂, NO₂,P(═O)(R²)₂, OSO₂R², OR², S(═O)R², S(═O)₂R², a straight-chain alkyl,alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched orcyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms,each of which may be substituted by one or more R² radicals, where oneor more nonadjacent CH₂ groups may be replaced by —R²C═CR²—, —C—C—,Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C═O, C═S, C═Se, C═NR², NR², P(═O)(R²),—C(═O)O—, —C(═O)NR²—, —O—, —S—, SO or SO₂ and where one or more hydrogenatoms may be replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R² radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R² radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R² radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R² radicals; or a combination of thesesystems; at the same time, two or more R¹ radicals together may form amono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; R² is the same or different at each instanceand is H, D, F, Cl, Br, I, B(OR³)₂, CHO, C(═O)R³, CR³═C(R³)₂, CN,C(═O)OR³, C(═O)N(R³)₂, Si(R³)₃, N(R³)₂, NO₂, P(═O)(R³)₂, OSO₂R³, OR³,S(═O)R³, S(═O)₂R³, a straight-chain alkyl, alkoxy or thioalkoxy grouphaving 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy orthioalkoxy group having 3 to 40 carbon atoms, each of which may besubstituted by one or more R³ radicals, where one or more nonadjacentCH₂ groups may be replaced by —R³C═CR³—, —C—C—, Si(R³)₂, Si(R³)₂,Ge(R³)₂, Sn(R³)₂, C═O, C═S, C═Se, C═NR³, NR³, P(═O)(R³), —C(═O)O—,—C(═O)NR³—, —O—, —S—, SO or SO₂ and where one or more hydrogen atoms maybe replaced by D, F, Cl, Br, I, CN or NO₂, or an aromatic orheteroaromatic ring system which has 5 to 60 aromatic ring atoms and maybe substituted in each case by one or more R³ radicals, or an aryloxy orheteroaryloxy group which has 5 to 60 aromatic ring atoms and may besubstituted by one or more R³ radicals, or an aralkyl or heteroaralkylgroup which has 5 to 60 aromatic ring atoms and may be substituted byone or more R³ radicals, or a diarylamino group, diheteroarylamino groupor arylheteroarylamino group which has 10 to 40 aromatic ring atoms andmay be substituted by one or more R³ radicals, or a combination of thesesystems; at the same time, two or more R² substituents together may alsoform a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic orheteroaromatic ring system; R³ is the same or different at each instanceand is H, D, F or an aliphatic, aromatic and/or heteroaromatichydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atomsmay also be replaced by F; at the same time, two or more R³ substituentstogether may also form a mono- or polycyclic, aliphatic,heteroaliphatic, aromatic or heteroaromatic ring system and n representsan integer in the range from 1 to
 20. 32. The compound according toclaim 24, wherein the difference between the index s in formula (LAr-1)and the index t in formula (LAr-2) is not more than
 2. 33. An oligomer,polymer or dendrimer containing one or more compounds according to claim20, wherein, rather than a hydrogen atom or a substituent, there are oneor more bonds of the compounds to the polymer, oligomer or dendrimer.34. A composition comprising at least one compound according to claim 20and at least one further compound selected from the group consisting offluorescent emitters, phosphorescent emitters, host materials, matrixmaterials, electron transport materials, electron injection materials,hole conductor materials, hole injection materials, electron blockermaterials and hole blocker materials.
 35. A formulation comprising atleast one compound according to claim 20 and at least one solvent.
 36. ATADF material, host material, electron transport material or holeconductor material which comprises the compound according to claim 20.37. A process for preparing a compound according to claim 20 whichcomprises joining a compound comprising at least one donor group to anacceptor group in a coupling reaction.
 38. An electronic devicecomprising at least one compound according to claim 20, wherein theelectronic device is selected from the group consisting of organicintegrated circuits, organic field-effect transistors, organic thin-filmtransistors, organic solar cells, organic optical detectors, organicphotoreceptors, organic field-quench devices, organic electroluminescentdevices.
 39. The electronic device as claimed in claim 38, wherein thedevice is an organic electroluminescent device selected from the groupof the organic light-emitting transistors, organic light-emittingdiodes, organic light-emitting electrochemical cells and organic laserdiodes.
 40. The compound as claimed in claim 20, wherein the compound isselected from the group consisting of Formula 3, Formula 4, Formula 7,Formula 8, Formula 28, Formula 29, Formula 32, Formula 43, Formula 44,Formula 45, Formula 46, Formula
 49. Formula 50 and Formula 51,


41. The compound as claimed in claim 40, wherein the compound isselected from the group consisting of Formula
 49. Formula 50 and Formula51.